CaRLaWinterSchool2012 Final Abstractbook

th
5 CaRLa Winter School

2012
Heidelberg
March 3-9, 2012
Final Program
Welcome to the 5th CaRLa Winter School
Welcome to the picturesque town of Heidelberg, welcome to CaRLa, the joint research
laboratory of BASF and University of Heidelberg and welcome to our CaRLa Winter School on
Homogeneous Catalysis!
With our Winter School, we aim to foster intense scientific exchange between established and
young researchers in the field of homogeneous catalysis.
The conference takes place from March 3-9, 2012 at the German-American-Institute downtown
Heidelberg, within walking distance to the old town.
Our scientific program consists of 1 Keynote Lecture, 10 lectures, 10 problem set sessions and
poster presentations.
The days are organized as a morning and afternoon session. Each session is divided into two parts;
the first part consists of a scientific lecture while the second part has a more educational focus.
Between the two sessions of the day, we have scheduled a prolonged lunch break for individual
use. In the evening, we have planned short poster presentations of selected poster contributions,
after which a light dinner is served in parallel with the poster sessions.
All presentations are scheduled to leave enough room for discussion and we encourage every
participant to use this time to make our Winter School an exciting event for science.
The conference is fully sponsored by BASF and we are happy to announce, that we will have the
opportunity for making an excursion to BASF on Thursday afternoon.
We hope that all participants will have a pleasant and scientifically stimulating stay in Heidelberg
during our Winter School.
If we can assist you in any way to make your stay in Heidelberg more pleasant, please do not
hesitate to contact us.
Michael Limbach Peter Hofmann

Programm of the CaRLa Winter School - Overview
All Sessions take place in the German-American-Institute Heidelberg

Saturday, 3rd March
until 16:00 Arrival and Coffee Break
16:30 Welcome Address Thomas Rausch

Prorector of Ruprecht Karls University,
Heidelberg
17:00 Key Note Lecture
Raw Material Change in the
Chemical Industry Friedhelm Balkenhohl, BASF SE
18:00 Light Dinner and Get-together
Sunday, 4th March
9:00 Training Session: Bond Activation with Perfluoroaryl Boranes Frustrated Lewis
Pairs and Catalysis
(Warren E. Piers)
10:00 Coffee Break
10:15 Lecture: Activation of CO and CO2 with Decamethylscandocinium-hydridoborate

Ion Pairs
(Warren E. Piers)
11:15 Coffee Break
11:30 Flash Poster Presentations
12:00 Lunch Break (free time)
14:30 Lecture: Sustainable and Atom-Efficient Catalytic Routes to Amines

(Dieter Vogt)
15:30 Coffee Break
15:45 Training Session: Ligand Control in Homogeneous Catalysis The Molecular

Machinery at Work
(Dieter Vogt)
16:45 Coffee Break
17:30 Poster Session including light dinner
Monday, 5th March
9:00 Lecture: The Ruthenium Chemistry of Olefin Metathesis

(Deryn E. Fogg)
10:00 Coffee Break
10:15 Training Session: Sustainable Metathesis

(Deryn E. Fogg)
11:15 Coffee Break
14:30 Lecture: Rational Ligand Design

(Bernd Straub)
15:30 Coffee Break

15:45 Training Session: Pitfalls in the Quantum-chemical Modelling of Catalytic Cycles
(Bend Straub)
16:45 Coffee Break
Tuesday, 6th March
9:00 Lecture: Well-defined supported catalysts via the controlled functionalization of

surfaces
(Christophe Copret)
10:00 Coffee Break
10:15 Training Session: Support effects in single-site catalysts: A molecular point of

view
(Christophe Copret)
11:15 Coffee Break
14:30 Lecture: Designing of Catalysts for Stereoregular Polymerization of Propylene

(Mosher Kol)
15:30 Coffee Break

15:45 Training Session: Development of Catalysts for the Synthesis of Poly(Lactic Acid)
and Related Materials
(Moshe Kol)
16:45 Coffee Break
Wednesday, 7th March
9:00 Lecture: Zinc Cluster Catalyzed Transesterification and Oxazoline Synthesis

(Kazushi Mashima)
10:00 Coffee Break
10:15 Training Session: Salt-free Reduction of Tantalum and Tungsten Halides for
Generating Low-valent Catalytically Active Species
(Kazushi Mashima)
11:15 Coffee Break
14:30 Training Session: Industrial Bioprocesses - Basic Principles

(Klaus Ditrich)
15:30 Coffee Break

15:45 Lecture: ChiProsTM - Optically Active Intermediates on an Industrial Scale
(Klaus Ditrich)
16:45 Coffee Break
Thursday, 8th March
9:00 Lecture: Palladium- and Nickel-Catalyzed Cross-Coupling Reactions of Alkyl

Electrophiles
(Gregory C. Fu)
10:00 Coffee Break
10:15 Training Session: Enantioselective Nucleophilic Catalysis

(Gregory C. Fu)
11:15 Coffee Break
14:30 Transfer to Ludwigshafen
15:00 Excursion of BASFs Main Site in Ludwigshafen
19:00 Winter School Dinner in Kulturbrauerei

Friday, 9th March
9:00 Lecture: Adding Aliphatic CH Bond Oxidations to Synthesis

(M. Christina White)
10:00 Coffee Break
10:15 Training Session: CH Oxidations and Organic Synthesis

(M. Christina White)
11:15 Coffee Break
11:30 Poster Prize Ceremony & Closing Remarks
12:00 Departure
Lectures & Training
Sessions
Raw Material Change in the Chemical Industry
Friedhelm Balkenhohl*
BASF SE, Synthesis and Homogeneous Catalysis, GCS M313, 67056 Ludwigshafen, Germany
e-mail: friedhelm.balkenhohl@basf.com
At each time availability and price structure of the fossil raw materials coal,
petroleum and natural gas have significantly influenced the technological basis and
consequently the buildup and development of the chemical industry. In the energy
industry a consistent raw material change from coal to oil and gas has occurred since the
middle of the 20th Century. The reason for this change lies mainly in the simpler
logistics as well as the versatile usefulness of oil and gas. Parallel to the change in the
energy industry the raw material base of the chemical industry has been changed from
coal to oil and gas. Olefins, which are produced mainly by steam cracking of naphtha,
and aromatic hydrocarbons, are still the crucial raw materials for the majority of the
value added chains of the chemical industry. Price volatility, regional distribution and
the finite reserves of crude oil are the main drivers for the development of conversion
technologies to utilize alternative raw materials, e.g. natural gas, coal, renewables and
carbon dioxide as feedstocks for the chemical industry.
Bond Activation with Perfluoroaryl BoranesFrustrated Lewis Pairs and
Catalysis
Jay Dutton, Adrian Y. Houghton, Adam Marwitz, Matt Morgan, Warren E. Piers,*a and
Masood Parvez,a
a
Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta, T2N
1N4 Canada.
e-mail: wpiers@ucalgary.ca
The activation of small molecules by Lewis acid/Lewis base combinations that form
very weak classical adducts is a recently exploited phenomenon in main group element
chemistry.[1] Because they dont quench each other through classical adduct formation,
they are known as frustrated Lewis pairs. This session will describe our groups
contributions to the development of FLPs and what is known regarding their
mechanism of action. Specifically, the role of Lewis acid strength in the reaction will be
discussed and methods of assessing Lewis acid strength will be presented. Finally, the
state of the art in FLP mediated catalysis will be surveyed.
[1] Stephan, D. W.; Erker, G. Angew. Chem. Int. Ed. 2010, 49, 46-77.
Activation of CO and CO2 with Decamethylscandocinium-hydridoborate Ion Pairs
Andreas Berkefeld,a Warren E. Piers,*a Masood Parvez,a Ludovic Castro,b Laurent
Maron,b and Odile Eisensteinc
a
Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta, T2N
1N4 Canada; bLPCNO, Universit de Toulouse, INSA, UPS, LPCNO, 135 avenue de Rangueil, F- 31077
Toulouse, France, and CNRS, LPCNO, F-31077 Toulouse, France ; cInstitut Charles Gerhardt, Universit
Montpellier 2, CNRS 5253, cc 1501, Place E. Bataillon, F-34095 Montpellier France
e-mail: wpiers@ucalgary.ca
As we have seen, frustrated Lewis pairs essentially provide a confined space

within which strong bonds can be activated with very low barriers. In some instances,
the components of the activated bond can be transferred to external substrates to close a
catalytic cycle, but these examples are relatively narrow in scope. Contact ion pairs
comprised of organotransition metal cations and weakly coordinating anions are similar
in character to these so-called FLPs, wherein the confined space between the ions may
possibly be utilized to activate small molecules. By analogy to the FLP systems, the
cation functions as the Lewis acid and the anion functions as the Lewis base; we
postulated that the potential for catalytic turnovers from such systems will be enhanced
due to the greater variety of reaction manifolds available to transition metals as opposed
to main group Lewis acids. We report here the use of the ion pair [Cp*2Sc]+[HB(C6F5)3]-
for the activation of CO and CO2. In the case of CO2, highly active catalysts for the
hydrosilation of CO2 to CH4 are obtained, while for CO, novel reactivity patterns for
coordinated CO are described. The mechanisms of both of these reactions were probed
experimentally and computationally and the results of these studies will be described.
Sustainable and Atom-Efficient Catalytic Routes to Amines
Dieter Vogt*
Technische Universiteit Eindhoven, Postbus 513, 5600 MB Eindhoven, The Netherlands
e-mail: d.vogt@tue.nl
Recent advances in the Rh-catalyzed hydroaminomethylation reaction (HAM), a

one-pot cascade of hydroformylation, condensation with an amine, and hydrogenation
towards amines, will be reported. Efficient catalyst and product separation can be
achieved by a two-phase approach using ionic liquids.[1],[2]
Furthermore, the highly efficient and selective Ru-catalyzed direct amination of
secondary (bio)alcohols with ammonia[3] towards primary amines will be discussed. In
this hydrogen shuttling approach protective groups are avoided and no additional
hydrogen is needed.
[1] B. Hamers, P. S. Buerlein, C. Mller, D. Vogt, Adv. Synth. Catal. 2008, 350, 332-
342.
[2] B. Hamers, E. Kosciusko-Morizet, C. Mller, D. Vogt, ChemCatChem 2009, 1,
103-106.
[3] D. Pingen, C. Mller, D. Vogt, Angew. Chem., Int. Ed. 2010, 49, 8130-8133.
Ligand Control in Homogeneous Catalysis The Molecular Machinery at Work
Dieter Vogt*
Technische Universiteit Eindhoven, Postbus 513, 5600 MB Eindhoven, The Netherlands
e-mail: d.vogt@tue.nl
In this session the major concepts and models used in homogeneous catalysis will be
discussed on the basis of selected practical examples and assignments, in which the
different concepts are at work in an as-pure-as-possible way. The scope and
limitations of models will be discussed. Attention will be paid to the delicate interplay
of all kind of factors that influence the activity, selectivity and stability of homogeneous
catalysts. Examples will come from the literature and from own research. An important
aspect of this session will be the way and the means employed to gain insight into the
mechanisms of homogeneous catalytic systems.
The Ruthenium Chemistry of Olefin Metathesis
Deryn E.Fogg*
Department of Chemistry, and Center for Catalysis Research & Innovation, University of Ottawa, Ottawa
ON, Canada K1N 6N5
e-mail: dfogg@uottawa.ca
Ruthenium metathesis catalysts are now widely recognized as powerful agents for
further, non-metathetical transformations.[1] In some cases, this expanded reactivity is
due to the action of the precatalyst and/or its alkylidene and/or methylidene derivatives:
in others, it reflects the operation of further ruthenium catalysts generated in situ,
whether by chance or design.[2] While a greater understanding of the underlying
inorganic transformations of these important complexes would clearly be advantageous,
overwhelming interest in their organic applications has tended to overshadow their
inorganic reaction chemistry. Many of their fundamental reactivity patterns thus remain
obscure. We will examine such pathways as they relate to inhibition or expansion of
opportunities in olefin metathesis.
[1] a) Alcaide, B.; Almendros, P.; Luna, A. Chem. Rev. 2009, 109, 3817-3858. b)
Alcaide, B.; Almendros, P. Chem. Eur. J. 2003, 9, 1259-1262.
[2] For tandem catalysis originating in metathesis catalysts, see: a) Shindoh, N.;
Takemoto, Y.; Takasu, K. Chem. Eur. J. 2009, 15, 12168-12179. b) Fogg, D. E.; dos
Santos, E. N. Coord. Chem. Rev. 2004, 248, 2365-2379. c) Wasilke, J.-C.; Obrey, S.
J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001-1020.
Sustainable Metathesis
Deryn E Fogg*
Department of Chemistry, and Center for Catalysis Research & Innovation, University of Ottawa, Ottawa
ON, Canada K1N 6N5
e-mail: dfogg@uottawa.ca
Olefin metathesis is attracting expanding interest as a means of harnessing renewable

resources. In particular, metathetical degradation of unsaturated plant oils has long been
regarded as a potential "alternative" route to -olefin feedstocks relevant to commodity
chemical applications. A major challenge, however, can be competing degradation of
the catalyst itself. We will examine the opportunities and limitations associated with use
of "functional-group tolerant" late-metal catalysts in these contexts.
Well-defined supported catalysts via the controlled functionalization of surfaces
Christophe Copret*
Department of Chemistry, ETH Zrich, W. Pauli Strasse, 10 CH-8093 Zrich, Switzerland
e-mail: ccoperet@ethz.ch
Controlling the chemistry at the surface of oxide materials has been a challenge for
forty years. In the first part of this lecture, we will discuss how it is possible to control
the OH density of the surface of silica and to exploit these surface functionalities to
generate well-defined surface metal complexes, which can then be used as precursor to
supported single-site catalysts.[1] We will then discuss the limitation of this approach,
and propose to extend it to developing silica supports with regularly distributed surface
organic functionalities, which correspond to the typical ligands of organometallic and
coordination chemistry.[2] We will also discuss how solid-state NMR spectroscopy
enables a detailed understanding of the structure of surface species in relation to their
catalytic performances.[3] The lecture will end with an open discussion on problems and
solutions.
[1] a) Copret et al. Angew. Chem. Int. Ed. 2003, 42, 156. b) Copret C. Dalton Trans.
2007, 5498. c) Gajan et al. New. J. Chem. 2011, 35, 2403.
[2] a) Maishal et al. Angew. Chem. Int. Ed. 2008, 47, 8654. b) Karam et al. Chem. Eur.
J. 2009, 15, 11820. c) Baffert et al. ChemSusChem. 2011, 4, 1762.
[3] a) Blanc et al. Coord. Chem. Rev. 2008, 37, 518. b) Gajan et al. Manuscript in
preparation.
Support effects in single-site catalysts: A molecular point of view
Christophe Copret*
Department of Chemistry, ETH Zrich, W. Pauli Strasse 10 CH-8093 Zrich, Switzerland
e-mail: ccoperet@ethz.ch
While the first lecture focused on silica-based materials, the second one will try to
elaborate on support effects in heterogeneous catalysis. In particular, it is well known
that changing the support from silica to alumina often significantly improved catalyst
performances of supported single-site catalysts for the hydrogenation, the metathesis
and the polymerization of alkenes.[1] The discussion will thus focus on understanding
what is alumina, in particular its surface functionalities as a function of thermal
treatment using probe molecules in a combined experimental and first principle
calculation approach. The nature and the role of surface functionalities will be discussed
in relation to the formation and the stabilization of surface active species.[2] The
lecture will end with an open discussion on the so-called support effects in
heterogeneous catalysis.
[1] Rascon et al. Chem. Sci. 2011, 2, 1449.

[2] a) Wischert et al. Chem. Commun., 2011, 47, 4890. b) Wischert et al. Angew. Chem.
Int. Ed., 2011, 50, 3202. c) Wischer et al. submitted.
Designing of Catalysts for Stereoregular Polymerization of Propylene
Moshe Kol*
School of Chemistry, Tel Aviv University, Ramat AvivTel Aviv 69978, Israel
e-mail: moshekol@post.tau.ac.il
Salalens are tetradentate dianionic sequential {ONNO}-type ligands that include

amine and imine internal neutral donors, and two peripheral anionic phenolate arms.
With the imine-donor and the amine-donor orienting their two neighboring donors in
meridional and facial geometries, respectively, the Salalens give rise to octahedral
complexes of group 4 metals of the type [{ONNO}MX2] having a fac-mer geometry
and C1-symmetry. In such complexes, the two monodentate labile groups are cis-related,
and reside in different steric and electronic environments.
We have recently developed an efficient methodology for the synthesis of Salalen
ligands that enables the fine-tuning of steric and electronic parameters. We found that
several titanium complexes of these ligands led to highly active catalysts for
polymerization of -olefins, and, most importantly, to polypropylene with very high
isotacticities, reaching [mmmm] > 99.6% and melting transitions of up to 169.9 C,
which is unprecedented, to our knowledge.[1],[2]
In this presentation we will describe the design principles that have led to this
development, and, as time allows, we will describe the breadth of the Salalen ligand
family, and the performance of Salalen complexes of other metals in propylene
polymerization.
[1] Press, K.; Cohen, A.; Goldberg, I.; Venditto, V.; Mazzeo, M.; Kol, M. Angew. Chem.
Int. Ed. 2011, 50, 3529.
[2] Sita, L. R. Angew. Chem. Int. Ed. 2011, 50, 6963.
Development of Catalysts for the Synthesis of Poly(Lactic Acid) and Related
Materials
Moshe Kol*
School of Chemistry, Tel Aviv University, Ramat AvivTel Aviv 69978, Israel
e-mail: moshekol@post.tau.ac.il
Poly(lactic acid) (PLA) is a biodegradable polymer derived from bio-renewable

resources having commodity-plastic and biomedical applications. PLA is synthesized by
the catalyzed ring opening polymerization (ROP) of lactide. Traditionally employed
homoleptic complexes such as tin octoate or aluminum isopropoxide catalyze the
polymerization of rac-lactide to give stereo-irregular polymers, however, catalysts
introduced in the last fisteen years that include metal complexes of polydentate ligands
enabled the synthesis of stereoregular PLA from rac-lactide and from meso-lactide. In
this presentation we will give some background on ring opening polymerization, and
describe several literature examples of catalysts leading to stereoregular polymerization
of lactide and related monomers.[1] We will also describe several recent examples from
our own work.[2]
[1] For several recent reviews, see: a) Dijkstra, P. J.; Du, H.; Feijen, J. Polym. Chem.
2011, 2, 520. b) Chisholm. M. H. Pure Appl. Chem. 2010, 82, 1647. c) Kiesewetter,
M. K.; Shin, E. J.; Hedrick, J. L.; Waymouth, R. M. Macromolecules 2010, 43,
2093. d) Stanford, M. J.; Dove, A. P. Chem. Soc. Rev. 2010, 39, 486. e) Thomas, C.
M. Chem. Soc. Rev. 2010, 39, 165. f) Platel, R. H.; Hodgson, L. M.; Williams, C. K.
Polym. Rev. 2008, 48, 11.
[2] a) Sergeeva, E.; Kopilov, J.; Goldberg, I.; Kol, M. Inorg. Chem. 2010, 49, 3977. b)
Stopper, A. L.; Okuda, J.; Kol, M. Macromolecules 2012, 45, 698.
Zinc Cluster Catalyzed Transesterification and Oxazoline Synthesis
Kazushi Mashima*
Department of Chemistry, Graduate School of Engineering Science,
Osaka University, Toyonaka, Osaka 560-8531, Japan.
e-mail: mashima@chem.es.osaka-u.ac.jp
The ester moiety represents one of the most ubiquitous functional groups in organic
compounds, serving as both key intermediate and protecting group in organic
transformations. Among various esterification reactions established so far, one of the
most convenient synthetic methods is transesterification, in which methyl or ethyl esters
react with various alcohols to give the corresponding esters in one step. Recently, we
developed m-oxo-tetranuclear zinc cluster Zn4(OCOCF3)6O as an efficiently catalyst for
transesterification, including chemoselective acylation of hydroxy group in the presence
of aliphatic amino group, catalytic acetylation of alcohols and catalytic deacetylation of
acetates. Because of mildness of the reaction conditions, these reactions have a high
degree of functional-group tolerance.[1]-[3] The catalytic synthesis of oxazoline by
treating esters and carboxylic acids with aminoalcohols is also delivered.
[1] Y. Maegawa, Y. Hayashi, T. Iwasaki, T. Ohshima, and K. Mashima, ACS Catalysis,

1, 1178-1182 (2011).
[2] T. Iwasaki, K. Agura, Y. Maegawa, Y. Hayashi, T. Ohshima, and K. Mashima, Chem.
Eur. J., 16, 11567-11571 (2010).
[3] T. Ohshima, T. Iwasaki, Y. Maegawa, A. Yoshiyama, and K. Mashima, J. Am. Chem.
Soc., 130, 2944-2945 (2008); Highlighted in Nature, 452, 415-416 (2008); Science,
319, 1163 (2008).
Salt-free Reduction of Tantalum and Tungsten Halides for Generating Low-valent
Catalytically Active Species
Kazushi Mashima*
Department of Chemistry, Graduate School of Engineering Science,
Osaka University, Toyonaka, Osaka 560-8531, Japan.
e-mail: mashima@chem.es.osaka-u.ac.jp
Low valent early transition metal complexes have been utilized as reagents and
catalysts for mediating bond formation reaction including olefin polymerization and
oligomerization and olefin metathesis reaction. Various reducing reagents have been
developed for reducing these metal halides; however, the complexation of the resulting
salt with the desired low-valent species hampered their isolation and lowered their
reactivity. Thus, we have developed a new methodology for generating salt-free
low-valent species by treating metal halides with
[1],[2]
3,6-bis(trimethylsilyl)-1,4-cyclohexadiene or its methyl derivative. The merit of this
reduction is no salt formation but produces 2 equiv of Me3SiCl, C6H5R (R = H or CH3).
The highlight of such methodology is that ligand-free Ta(III) species catalyzes the
trimerization of ethylene to 1-hexene with >98% selectivity without any detection of
internal olefins through a metallacycle mechanism.[2] In this lecture, a personal
approach how to propose any idea is described.
[1] H. Tsurugi, T. Saito, H. Tanahashi, J. Arnold, and K. Mashima, J. Am. Chem. Soc.,
133, 18673-18683 (2011).
[2] R. Arteaga-Mueller, H. Tsurugi, T. Saito, M. Yanagawa, S. Oda, and K. Mashima, J.
Am. Chem. Soc., 131, 5370-5371 (2009).
Palladium- and Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Electrophiles
Gregory C. Fu*
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Room 18-290,
Cambridge, MA 02139-4307 USA
e-mail: gcf@mit.edu
Despite the tremendous accomplishments that have been described in the

development of palladium- and nickel-catalyzed carboncarbon bond-forming processes,
it is nevertheless true that many significant opportunities remain. For example, to date
the overwhelming majority of studies have focused on couplings between two
sp2-hybridized reaction sites (e.g., an aryl metal with an aryl halide).
As of 2001, there were relatively few examples of palladium- or nickel-catalyzed
coupling reactions of alkyl electrophiles. During the past several years, we have pursued
the discovery of palladium- and nickel-based catalysts for coupling activated and
unactivated primary and secondary alkyl electrophiles that bear hydrogens. Our recent
efforts to develop broadly applicable methods, including enantioselective processes,
will be discussed.
Enantioselective Nucleophilic Catalysis
Gregory C. Fu*
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Room 18-290,
e-mail: gcf@mit.edu
Nucleophiles such as 4-(dimethylamino)pyridine (DMAP) and tertiary phosphines

catalyze a wide array of useful and interesting reactions. We are pursuing the development
of asymmetric processes catalyzed by enantiopure DMAP derivatives and phosphines.
Adding Aliphatic C-H Bond Oxidations to Synthesis
M. Christina White*
Department of Chemistry, University of Illinois, 270 Roger Adams Laboratory, 600 South Mathews Ave.,
Urbana, IL 61801, USA
e-mail: white@scs.uiuc.edu
Aliphatic C-H oxidations have appeared in the literature sporadically over the past
century. However, synthetic chemists considered these transformations to be too poorly
selective and/or reactive for routine utilization in synthesis. As recently as 2007, chemists
considered bio-inspired catalysts with elaborate binding pockets to be the most promising
candidates for achieving site-selectivity for intermolecular reactions with unactivated,
aliphatic C-H bonds. Reactivity differences between these very inert bonds were thought to
be too minor for a small molecule catalyst to discriminate effectively. Remarkably, only
four years after this sentiment pervaded, it is now widely accepted that predictable
selectivity and good reactivity for aliphatic C-H oxidations is possible with electrophilic
small molecule catalysts and simple organic reagents.
Three factors have that have been crucial to this paradigm shift in how the reactivity of
C-H bonds is viewed will be discussed: first, the discovery of a selective Fe(PDP) catalyst
that operates under synthetically useful conditions (limiting substrate) and reliably
furnishes 50% isolated yields of mono-oxidized products; second, the systematic
delineation of predictable rules for the selectivities observed that are generalizable to
other electrophilic oxidants; and, third, the demonstration that these rules persist in diverse,
complex molecule settings. Perhaps the most important finding with Fe(PDP) is that the
same selectivity rules that govern the differential reactivity of traditional functional groups
(i.e., electronics, sterics, and stereoelectronics) also govern the reactivity of relatively inert
C-H bonds.
CHOxidationsandOrganicSynthesis
M.ChristinaWhite*
Department of Chemistry, University of Illinois, 270 Roger Adams Laboratory, 600 South Mathews Ave.,
e-mail: white@scs.uiuc.edu

Among the frontier challenges in chemistry in the 21st century are the
interconnected goals of increasing control of chemical reactivity and synthesizing
stereochemicallyandfunctionallycomplexmoleculeswithhigherlevelsofefficiency.
Althoughithasbeenwelldemonstratedthatgivenampletimeandresources,highly
complex molecules can be synthesized in the laboratory, too often current reaction
manifoldsdonotallowchemiststomatchtheefficiencyachievedinNature.
Traditional organic methods for installing oxidized functionality rely heavily on

acidbase reactions that require extensive functional group manipulations (FGMs)
including wasteful protectiondeprotection sequences. Due to their ubiquity in
complex molecules and inertness to most organic transformations, CH bonds have
typically been ignored in the context of methods development for total synthesis.
Discovery and development of highly selective oxidation methods for the direct
installation of oxygen, nitrogen and carbon into allylic and aliphatic CH bonds of
complex molecules and their intermediates are discussed. Unlike Nature which uses
elaborate enzyme active sites, this chemistry harnesses the subtle electronic, steric,
and stereoelectronic interactions between CH bonds and small molecule transition
metal complexes to achieve high regio, chemo, and stereoselectivities. Our current
understandingoftheseinteractionsgainedthroughempiricalandmechanisticstudies
willbediscussed.Novelstrategiesforstreamliningtheprocessofcomplexmolecule
synthesisenabledbythesemethodswillbepresented.Collectively,ourprogramaims
tochangethewaythatcomplexmoleculesareconstructedbydefiningtheprinciples
thatgovernreactivityofCHbondsincomplexmoleculesettings.
Poster Abstracts
Poster 1
CaRLa The Catalysis Research Laboratory Catalyzing the Cooperation Between

Science and Industry
Peter Hofmann,a,b* Michael Limbacha,c*
a
Catalysis Research Laboratory, Im Neuenheimer Feld 584, 69120 Heidelberg, Germany; b
Organisch-Chemisches Institut der Universitt Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg,
Germany; c BASF SE, GCS/C M313, 67056 Ludwigshafen, Germany
e-mail: ph@oci.uni-heidelberg.de, michael.limbach@basf.com
Innovation is an intersectoral topic. In this regard, public private partnerships are key
instruments for improving a countrys innovativeness.
CaRLa is a new role model of research cooperation, in which BASF and the
University of Heidelberg work closely together in a joint laboratory. In CaRLa, 6
postdocs of the university, supervised by Heidelberg faculty, together with 6 postdocs
directed by BASF research units are working bench to bench to investigate basic
research issues directed towards potential industrial applications in the field of transition
metal based homogeneous catalysis. The goal of CaRLa is to facilitate the transfer of
results from basic research towards applications in industry.
Catalysis is the most important chemical technology of the chemical industry. More
than 80 percent of all chemical products come into contact with catalysts at least once
during their synthesis. Research in the field of homogeneous catalysis without doubt has
resulted in an exceptional track record of real innovations. Its potential spans a wide
range from polymerization to hydroformylation, carbonylation, asymmetric
hydrogenation, carbon-carbon or carbon-heteroatom bond formation to applications of
homogeneously catalyzed metathesis.
In CaRLa, industry and academia jointly have identified interesting fields of research
and challenging targets. CaRLa utilizes the expertise of its principal investigators to
optimize a focused research portfolio covering contemporary topics of transition metal
based homogeneous catalysis.
Poster 2
The Total Synthesis of Spirastrellolide A Methyl Ester

Alexander Arlt, Alois Frstner*
Max-Planck-Institut fr Kohlenforschung
e-mail: arlt@mpi-muelheim.mpg.de
Spirastrellolide A Methyl Ester was isolated in 2003 from the Carribean marine sponge
spirastrella coccinea as the first member of a family of macrolide natural products
(Spirastrellolides A-G).[1] The Spirastrellolides consist of a 47 membered polyketide backbone
and exhibit outstanding biological activity.
In 2008 Paterson et al. published the first total synthesis of Spirastrellolide A Methyl Ester
followed shortly thereafter by the reports of our group on the total synthesis of Spirastrellolide F
Methyl Ester.[2] Due to the high convergency of
our synthetic strategy small changes to the
fragments extend it to the total synthesis of
Spirastrellolide A, the initial target of our synthetic
efforts. In our successful approach towards
Spirastrellolide A a dithiane at the C16 position (a
ketone equivalent) was used for fragment coupling.
The corresponding ketone could then be
transformed at a late stage into the C15-C16
double bond by an efficient two step sequence, giving the core of Spirastrellolide A. Direct
attachment of the side chain via Julia-Kocienski olefination completed our Total Synthesis of
Spirastrellolide A Methyl Ester.[3]
[1] Andersen et al. JACS 2003, 125, 5296 and JOC 2007, 72, 9842.
[2] a) Paterson et al. ACIE 2008, 47, 3016 and ACIE 2008, 47, 3021; b) Frstner et al.
ACIE 2009, 48, 9940 and ACIE 2009, 48, 9946; c) 2nd generation: Frstner et al.
ACIE 2011, 50, 8739; Paterson et al. ACIE 2012, DOI: 10.1002/anie.201108594.
[3] A. Arlt, A. Frstner, 2012, manuscript in preparation.
Poster 3
Auto-Tandem Catalysis with Ruthenium: Remote Hydroesterification of Olefins

Nicolas Armanino, Erick M. Carreira*
Laboratorium fr Organische Chemie, ETH Zrich, CH-8093 Zrich, Switzerland.
e-mail: carreira@org.chem.ethz.ch
One-pot processes that involve cascading reactions provide attractive tools for
organic synthesis by simplifying operations and reducing the number of required
intermediate isolations. Of particular interest are reactions that use a single catalytic
entity capable of promoting multiple distinct steps without the need for operator
intervention. In the course of our investigations, we have developed an auto-tandem
catalytic system for the isomerization-hydroesterification sequence of internal olefins.
The system is based on low-valent ruthenium carbonyl clusters, enabling the

incorporation of a C1-unit by C-C bond formation onto a broad scope of allylic amines
and alcohols. The process is characterized by operational simplicity, results in the
functionalization of a remote position of the substrate and permits easy access to chiral
lactone and lactam building blocks. Our mechanistic working model suggests that the
key to success in this cascade is the formation of an active ruthenium cluster hydride by
metal protonation, capable of promoting fast olefin isomerization that prevails over
undesired decarbonylation pathways.
Poster 4
Highly Modular Synthesis of P-chiral NHCP Ligands for Rhodium-Catalyzed

Asymmetric Hydrogenation
Marcel Brill, Patrick Hanno-Igels, Peter Hofmann*
Organisch-Chemisches Institut, Universitt Heidelberg, INF 270, D-69120 Heidelberg, Germany
e-mail: ph@oci.uni-heidelberg.de
In spite of numerous highly efficient and selective catalysts that have been prepared
for rhodium-catalyzed asymmetric hydrogenation, the development of ligands which
can be conveniently synthesized and easily modified continues to be an important issue
in order to selectively hydrogenate a wide variety of substrates.[1] We have recently
developed an efficient synthesis of sterically bulky and electron-rich N-phosphino-
methyl functionalized N-heterocyclic carbenes that allows facile tuning of steric and
electronic properties of the ligands.[2] Here, we present our new highly modular
synthetic approach to P-chiral N-phosphinomethyl substituted NHCs of type 1 and our
first results related to the synthesis of catalysts bearing ligands 1 and 2 and their
performance in asymmetric hydrogenation.[3]
[1] a) Y. Chi, W. Tang, W. Zhang in Modern Rhodium-Catalyzed Organic Reactions

(Ed.: P. A. Evans), Wiley-VCH, Weinheim, 2005, 1.
[2] a) U. Herrlich (ne Blumbach), Dissertation, Universitt Heidelberg 2007; b) P.
Hofmann, P. Hanno-Igels, O. Bondarev, C. Jkel, WO 2009/10116 (A2).
[3] a) M. Brill, ongoing Dissertation, Universitt Heidelberg; b) C. Jkel, P. Hofmann,
C. Scriban, P. Hanno-Igels, WO 2011/012687 (A1).
Poster 5
New Concepts for Ruthenium-Catalyzed Olefin Metathesis Reactions

Jos Cabrera,a Robin Padilla,a Kristina Wilckens,a Peter Hofmann,*a,b Michael
Limbach*a,c
a
Catalysis Research Laboratory (CaRLa), Im Neuenheimer Feld 584, 69120 Heidelberg, Germany;
b
Organisch-Chemisches Institut, Ruprecht-Karls-Universitt Heidelberg, Im Neuenheimer Feld 270,
69120 Heidelberg, Germany; cBASF SE, Synthesis and Homogeneous Catalysis, GCS/C, M313, Carl
Bosch Strae 38, 67056 Ludwigshafen, Germany
e-mail: ph@oci.uni-heidelberg.de, michael.limbach@basf.com
Homogenous catalysts capable of strongly binding to a solid support in active form

and without the need for extensive synthetic manipulations of the catalyst or support,
are attractive from an industrial perspective. Building on previous work with high silica
affinity Ru-complexes[1] and subsequent high-throughput studies,[2] we developed and
studied a new class of heterogeneous catalysts consisting of NHC-modified Ru-
complexes adsorbed on to silica. The Ru complexes were immobilized via a simple
solvent transfer procedure and tested in a variety of olefin metathesis reactions under
continuous flow conditions. These new complexes exhibited substantially higher
activities compared to Re2O7, a classical, state of the art heterogeneous metathesis
catalyst.
While ruthenium complexes with phosphorus-based ligands in the trans geometry
are the most commonly encountered, previous work has shown that chelating cis
bisphosphane ligands used with cationic ruthenium complexes exhibit significantly
enhanced catalytic activity in ROMP reactions.[3] As such, another area of study is
focused on the synthesis of Ru-carbene complexes incorporating new, chelating cis
phosphinomethyl substituted NHC ligands for use in ROMP reactions.
[1] J. A. Schachner, J. Cabrera, R. Padilla, C. Fischer, P. A. van der Schaaf, R. Pretot, F.

Rominger, M. Limbach, ACS Catal. 2011, 1, 872-876.
[2] J. Cabrera, R. Padilla, R. Dehn, S. Deuerlein, . Guajski, E. Chomiszczak, J. H.
Teles, M. Limbach, K. Grela, Adv. Synth. Catal. 2012, in press.
[3] S. M. Hansen, M. A. O. Volland, F. Rominger, F. Eisentrager, P. Hofmann, Angew.
Chem. Int. Ed. 1999, 38, 1273-1276.
Poster 6
The Synthesis of a New Class of Chiral Pincer Ligands and Their Applications in
Enantioselective Catalysis
Qing-Hai Deng, Hubert Wadepohl, Lutz H. Gade*
Anorganisch-Chemisches Institut, Universitt Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg,
Germany
e-mail: lutz.gade@uni-hd.de
A new class of chiral tridentate N-donor pincer ligands, bis(oxazolinyl-

methylidene)isoindolines (boxmi) has been synthesized in three steps starting from
readily available phthalimides.1
These ligands were subsequently applied in the Ni-catalyzed enantioselective

fluorinations and the Cr-catalyzed enantioselective Nozaki- Hiyama-Kishi reaction to
obtain the corresponding products with high enantioselectivities.[1] Recently, we
reported the Cu-catalyzed enantioselective alkylation of -ketoesters using alcohols for
the in situ preparation of alkylating reagents.[2] The alkylation products derived from
2-substituted allylic alcohols or their corresponding iodides were subsequently
converted to spirolactones, bi-spirolactones and related chiral target products.
[1] Deng, Q.-H.; Wadepohl, H.; Gade, L. H. Chem. Eur. J. 2011,17, 14922.
[2] Deng, Q.-H.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2012, DOI:
10.1021/ja211859w.
Poster 7
The Role of Metal-Hydroxide Complexes in Late-Transition Metal Mediated

Transmetalation Reaction: The Case of Gold
Stphanie Dupuy, Luke Crawford, Michael Buhl, Alexandra M. Slawin, Steven P.
Nolan*
EASTCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK
e-mail: sd53@st-andrews.ac.uk
Metal-catalyzed cross-coupling reactions are commonly employed as a powerful

synthetic tool for the formation of C-C bonds and among them the Suzuki-Miyaura
reaction plays a prominent role.[1] A key step in this reaction features the transmetalation
of a boron reagent to palladium. Although, this step has been extensively studied, the
actual reaction sequence involved is still a matter of debate.[2] Very recent results
reported by Hartwig[3] and Amatore and Jutand[4] support a hypothesis where the
transmetalation reaction involves a palladium hydroxide reacting with the boronic acid.
In our search for new reactions with (NHC)-gold(I) complexes, we have developed an
improved synthetic protocol for the transmetalation reaction between arylboronic acids
on [Au(NHC)]-type complexes and have recently examined whether the intriguing
observation of the intermediacy of a metal-hydroxide complex might also exist in d10
systems.[5]
[1] N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.

[2] M.-E. Moret, D. Serra, A. Bach, P. Chen, Angew. Chem. Int. Ed. 2010, 49,
2873-2877.
[3] J. F. Hartwig, B. P. Carrow, J. Am. Chem. Soc. 2011, 133, 2116-2119.
[4] C. Amatore, A. Jutand, G. Le Duc, Chem. Eur. J. 2011, 17, 2492-2503.
[5] Manuscript submitted.
Poster 8
PNS-type Ruthenium Pincer Complexes

Moti Gargir, Gregory Leitus,b Linda J.W. Shimon,b Yehoshua Ben-David,a David
a
Milsteinb*
a
Department of Organic Chemistry, bDepartment of Chemical Research Support, Weizmann Institute of
Science, Rehovot 76100, Israel
e-mail: motig@weizmann.ac.il
Dearomatized pincer complexes (PNN)Ru(H)CO 1 and (PNP)Ru(H)CO 2, which

were reported by our group catalyze several green catalytic reactions. 1 is an efficient
catalyst for the dehydrogenative coupling of alcohols to esters, acylation of secondary
alcohols by esters with dihydrogen liberation, direct dehydrogenative coupling of
alcohols and amines to form amides.[ 1 ] Unlike 1, complex 2 catalyzes the
dehydrogenative coupling of alcohols and amines to generate imines, rather than
amides.[2] Apparently, modification of the pincer arm has a profound effect on
catalytic activity. The thioether arm of PNS complexes is expected to be
hemilabile[3]-[5] but, unlike the PNN ligand, it lacks the ability to serve as a base. Here
we present new pincer ruthenium complexes based on a new PNS ligand, including
their synthesis, reactivity and catalytic activity.
[1] Gunanathan, C.; Milstein, D. Accounts Chem. Res. 2011, 44, 588-602.
[2] Milstein, D.; Gnanaprakasam, B.; Zhang, J. Angew. Chem. Int. Edit. 2010, 49,
1468-1471.
[3] Vinas, C.; Angles, P.; Sanchez, G.; Lucena, N.; Teixidor, F.; Escriche, L.; Casabo, J.;
Piniella, J.; Alvarez- Larena, A.; Kivekas, R.; Sillanpaa, R. Inorg. Chem. 1998, 37
701-707.
[4] Canovese, L.; Visentin, F.; Chessa, G.; Uguagliati, P.; Santo, C.; Bandoli, G.; Maini,
L. Organometallics 2003, 22, 3230-3238.
[5] Bassetti, M.; Capone, A.; Salamone, M. Organometallics 2004, 23, 247-252.
Poster 9
Diastereoselective Synthesis of Tricyclic Indolizine Alkaloids Using

En-Yne-En-RRM RCM Cascade
Matthias T. Grabowski, Siegfried Blechert*
TU Berlin Berlin Institute of Technology, Institute of Chemistry, Str. des 17. Juni 115, D-10623 Berlin
e-mail: blechert@chem.tu-berlin.de
Ring-rearrangement metathesis has proven to be a powerful synthetic tool for the

construction of carbo- and heterocycles and has been efficiently applied to various
natural product syntheses of diverse polycyclic systems. A cascade reaction with a
diastereoselective En-Yne-En-RRM RCM as a key step has been developed for the
synthesis of tricyclic indolizines.
R [Ru]
HX
[Ru]
N X
N N
H
R R
HX: p-TsOH, TfOH,
d-RRM RCM
HBF4 or etc.
Dienynes turned out to be challenging substrates for tandem metathesis processes,

due to a lack of selectivity-controlling groups. A rational design for the desired pathway
is shown within this work: a cyclic ene subunit with a triple bond in an appropriated
distance for a favored RRM, and a R-group which is not diminishing the catalyst
activity, for the post-RRM RCM, offer perfect reaction control and avoid undesired side
pathways.
This attractive and protecting-group-free route can be easily used for the synthesis of
lepadiformine/ cylindricine or other izidine alkaloids.
Poster 10
Theoretical Investigations on an Iron Catalyzed Alkylation Reaction

Berit Heggen, G. Gopakumar, Walter Thiel*
Max-Planck-Institut fr Kohlenforschung, Kaiser-Wilhelm-Platz 1,
45470 Mlheim an der Ruhr, Germany
e-mail: heggen@kofo.mpg.de
Cross-coupling reactions are well-established in synthetic chemistry. But one major

drawback is the use of expensive, e.g. palladium, catalysts. Therefore, iron got into
focus as a cheap and benign metal to assist cross-coupling reactions.[1] Organolithium
compounds in conjunction with iron halides proved to be suitable. However, the
mechanistic details and nature of possible reaction intermediates are yet to be
confirmed.[2] In this regard, the recent synthesis and structural characterization of an
organoferrate complex 1 by Frstner and co-workers, has opened up new directions.[3]
Two possible mechanistic pathways have been proposed for alkylation reactions by
the use of 1: a substitution mechanism and a "classical" oxidative addition/reductive

elimination pathway. In this context, we have applied Density Functional Theory (DFT)
methodologies to gain further insights.
[1] Sherry, B. D.; Frstner, A. Acc. Chem. Res. 2008, 41, 1500.
[2] Kauffmann, T, Angew. Chem. Int. Ed. 1996, 35, 386-403.
[3] Frstner, A.; Martin, R.; Krause, H.; Seidel, G.; Goddard, R.; Lehmann, C. W. J.
Am. Chem. Soc. 2008, 130, 8773-8787.
Poster 11
N-Heterocyclic Carbene Complexes and their Catalytic Activity

Christoph Hubbert, A. Stephen K. Hashmi*
Ruprecht-Karls-Universitt Heidelberg, Organisch-Chemisches Institut,
Im Neunheimer Feld 270, D-69124 Heidelberg, Germany
e-mail: chubbert@oci.uni-heidelberg.de
N-heterocyclic carbene complexes of different metals are well established catalysts

for several reactions in academic and industrial laboratories.[1],[2] A typical synthesis of
such complexes is often a multi-step procedure via an imidazolium salt and a
transmetallation step. Hence, a short and efficient route towards high active catalysts
would be very useful.
On my poster I present an easy route towards N-heterocyclic carbene complexes

starting from easily accessible metal isocyanide complexes of several transition
metals.[3]
Furthermore, the results of catalytic test reactions which show the exceptional
activity of the catalyst, will be presented.
[1] Cazin, C.S.J., N-Heterocyclic Carbenes in Transition Metal Catalysis and

Organocatalysis, Heidelberg, London, New York: Springer 2011.
[2] Nolan, S.P., N-Heterocyclic Carbenes in Synthesis, Weinheim: Wiley-VCH 2006.
[3] Hashmi, A.S.K.; Lothschtz, C.; Bhling, C.; Hengst, T.; Hubbert, C.; Rominger, F.
Adv. Synth. Catal. 2010, 352, 30013012.
Poster 12
Triflic Acid Catalyzed Diacetoxylation of Alkenes

Yan-Biao Kanga, Lutz H. Gade*a,b
a
Catalysis Research Laboratory (CaRLa), Im Neuenheimer Feld 584, 69120 Heidelberg, Germany
b
Anorganisch-Chemisches Institut, Universitt Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg,
Germany
e-mail: lutz.gade@uni-hd.de
Clean and efficient diacetoxylation reactions of alkenes catalyzed by triflic acid

using commercially available (Diacetoxyiodo)benzene or peroxyacids as oxidants were
presented.[1],[2] Mechanisms based on experimental evidence were also described.
[1] Kang, Y.-B.; Gade, L. H. J. Am. Chem. Soc. 2011, 133, 3658.
[2] Kang, Y.-B.; Gade, L. H. J. Org. Chem. 2012, 77, 1610.
Poster 13
Stereocontrolled Ring-Opening-Polymerization of Lactide Monomers by

Bis(phenolato) Rare-Earth Metal Initiators
Andreas Kapelskia, Jean-Charles Buffetb, Jun Okudaa*
a
Institut fr Anorganische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, bChemistry
Research Laboratory, Mansfield Road, Oxford, OX1 3TA (UK)
e-mail: Jun.Okuda@ac.rwth-aachen.de
Monomeric rare-earth metal bis(dimethylsilylamido) complexes bearing an (OSSO)-

type chelating bis(phenolato) ligand [(OSSO)Ln{N(SiMe2H)2}(THF)] (Ln = Sc, Y)
were isolated from amine elimination reaction by rare-earth metal
tris{bis(dimethylsilylamido)} precursors [Ln{N(SiMe2H)2}3(THF)x] (Ln = Sc, x = 1; Ln
= Y, x = 2) with one equivalent of tetradentate (OSSO)-type bis(phenol).
Scheme 1: Synthesis of rare-earth metal bis(dimethylsilylamido) complexes.

These rare-earth metal initiators polymerize rac-lactide to heterotactic polylactide
(PLA) and meso-lactide to highly syndiotactic PLA. The variation of the bridge
(flexible or rigid, chiral or achiral) has been studied to their influence on the level of
tacticity of the meso- or rac-polylactides.
[1] J.-C. Buffet, A. Kapelski, J. Okuda, Macromolecules 2010, 43, 10201 10203.
[2] A. Kapelski. J.-C. Buffet, T. P. Spaniol, J. Okuda, Chem. Asian J., DOI:
10.1002/asia.201100826.
Poster 14
Mechanochemical Degradation of Lignin Model Compounds

T. Kleine, J. Buendia, J. Mottweiler, E. Zuidema, C. Bolm*
Institute of Organic Chemistry, Landoltweg 1, D-52056 Aachen, Germany
e-mail: Tillmann.Kleine@oc.RWTHAachen.de; Carsten.Bolm@oc.RWTHAachen.de
Lignin is a potentially cheap and substantial source for platform chemicals or

combustion engine fuel additives[1] although its exploitation suffers from high technical
barriers.[ 2 ] Poor solubility and structural diversity of lignin are the most critical
obstacles for chemical conversion.[3],[4] In respect to this challenging, highly complex
substrate, advanced reaction techniques such as ball milling are expedient.[5]
We now present a protocol which allows the efficient and selective cleavage of
-O-4-linkage model compounds[6] by use of cheap bulk reagents under organocatalytic
conditions and without solvent, inert gas atmosphere or external sources of heat in the
ball mill. The model compounds, which are accessible in a three step synthesis, are
treated with sodium hydroxide in the presence of DMAP in the ball mill to give
phenolic and acetophenone derived degradation products in good yield.
[1] J. C. Hicks, J. Phys. Chem. Lett. 2011, 2, 2280 2287.

[2] J. Zakzeski, P. C. Bruijnincx, A. L. Jongerius, B. M. Weckhuysen, Chem. Rev. 2010,
110, 3552 3599.
[3] M. Lawoko, A. R. P. van Heiningen, J. Wood Chem. Tech. 2011, 31, 183 203.
[4] D. Takada, K. Ehara, S. Saka, J. Wood Sci. 2004, 50, 253 259.
[5] S. L. James, C.J. Adams, C. Bolm, D. Braga, P. Collier, T. Frii, F. Grepioni, K. D.
M. Harris, G. Hyett, W. Jones, A. Krebs, J. Mack, L. Maini, A. G. Orpen, I. P. Parkin,
W. C. Shearouse, J. W. Steed, D. C. Waddell, Chem. Soc. Rev. 2012, 41, 413 447.
[6] J. Buendia, J. Mottweiler, C. Bolm, Chem. Eur. J. 2011, 17, 13877 13882.
Poster 15
Palladium-Catalyzed Cross-Coupling Reactions and Direct

CH Bond Functionalizations
Christoph Kornhaa, Lutz Ackermann*
Institut fr Organische und Biomolekulare Chemie, Georg-August-Universitt Gttingen, Tammanstr. 2,
37077 Gttingen, Germany
e-mail: Lutz.Ackermann@chemie-uni-goettingen.de
Heteroatom-substituted secondary phosphine oxides (HASPO) have emerged as

efficient preligands for transition metal-catalyzed cross-coupling reactions.[1],[2] Recently,
we synthesized well-defined air-stable palladium complexes derived from
(HA)SPO-preligands, which turned out to be versatile catalysts for efficient
Kumada-Corriu cross-coupling reactions of unactivated (hetero)aryl- and alkenyl
tosylates with an improved catalytic activity as compared to the corresponding in-situ
generated catalysts.[3]
Moreover, these complexes were found to be highly active catalysts in

environmentally benign direct CH Bond functionalizations of various azoles.[4],[5]
[1] L. Ackermann, Synlett 2007, 507526.

[2] L. Ackermann, Isr. J. Chem. 2010, 50, 652663.
[3] a) L. Ackermann, A. Althammer, Org. Lett. 2006, 8, 34573460; b) L. Ackermann,
H. K. Potukuchi, A. R. Kapdi, C. Schulzke, Chem. Eur. J. 2010, 16, 33003303.
[4] L. Ackermann, A. R. Kapdi, S. Fenner, C. Kornhaa, C. Schulzke, Chem. Eur. J.
2011, 17, 29652971.
[5] L. Ackermann, S. Barfer, C. Kornhaa, A. R. Kapdi, Org. Lett. 2011, 13,
30823085.
Poster 16
Investigation of Fundamental Steps in the Formation of Acrylates from CO2 and

Ethylene
Michael Lejkowski, Ronald Lindner, Takeharu Kageyama,a Philipp-Nikolaus Plessow,a
a a
Stephan Schunk,b Michael Limbacha,c*

a
CaRLa - Catalysis Research Laboratory, Im Neuenheimer Feld 584, D-69120 Heidelberg, Germany; bhte
Aktiengesellschaft, Kurpfalzring 104, D-69123 Heidelberg, Germany; cBASF SE, Synthesis and
Homogeneous Catalysis, GCS/C M313, Carl-Bosch-Strasse 38, D-67056 Ludwigshafen, Germany
e-mail: michael.lejkowski@carla-hd.de, michael.limbach@basf.com
Sodium acrylate is the main component of common superabsorbents. Its direct

synthesis via oxidative coupling of CO2 and ethylene would offer an interesting
O
alternative to the industrial process currently
ONa LnNi0
utilized. Nickelalactones (1), reported in the CO2 +
[1]
revolutionary works of Hoberg, were frequently ligand
exchange
oxidative
coupling
discussed as possible intermediates in a hypothetic O
catalytic synthesis of acrylic acid[2] and its ONa NiLn 1
L nNi0 O
derivatives (Figure 1). In order to develop a process O
for catalytic formation of acrylates from CO2 and reductive H
elimination -hydride
ethylene a wide spectrum of ligands and additives is NiLn elimination
O
currently investigated, with both experimental and NaOH
O
quantum chemical methods.
[1] Hoberg, H.; Peres, Y.; Krger, C.; Tsay, Y.H. Angew. Chem. Int. Ed. 1987, 26,
771-773.
[2] Fischer, R.; Langer, J.; Malassa, A.; Walther, D.; Grls, H.; Vaughan, G. Chem.
Commun. 2006, 23, 2510-2512.
Poster 17
Ring opening polymerization of Propyleneoxid by N-Heterocyclic Carbene

Precursor
Ronald Lindner, Michael Lejkowski,a Peter Deglmann,b Kerstin Wiss,c Michael
a
Limbacha,d*
a
CaRLa Catalysis Research Laboratory, Im Neuenheimer Feld 584, 69120 Heidelberg, Germany,
b
BASF SE, GMC/M B1, 67056 Ludwigshafen, Germany, cBASF SE, GMU/A B1, 67056
Ludwigshafen, Germany, dBASF SE, GCS/C M313, 67056 Ludwigshafen, Germany
e-mail: ronald.lindner@carla-hd.de, michael.limbach@basf.com
Over the last decade NHC catalysts for the ROP of cyclic esters gathered
considerable attention.[ 1 ] However, the application of NHCs for the ring-opening
polymerization of epoxides is significantly less investigated.[2] Within this work we
demonstrate the application of N-heterocyclic
carbenes adducts with CO2 (NHC-CO2) for the NHC-pr ecur sor:
R1 N N R2
ring-opening polymerization of propyleneoxide
CO2
(PO) under industrially relevant conditions.
T CO2
A further objective of this work was the
investigation of the structure-activity relationship of cat.: NHC
the NHC scaffold. Additional new insights in the R OH + O R

O
OH
n
mechanism of this reaction were obtained.
[1] a) Kamber, N. E.; Jeong, W.; Waymouth, R. M. Chem. Rev. 2007, 107, 58135840.
b) Kiesewetter, M. K.; Shin, E. J.; Hedrick, J. L.; Waymouth, R. M.
Macromolecules 2010, 43, 20932107.
[2] a) Raynaud, J.; Ottou, W. N.; Gnanou, Y.; Taton, D. Chem. Commun. 2010, 46,
32033205. b) Raynaud, J.; Absalon, C.; Gnanou, Y.; Taton, D. Macromolecules
2010, 43, 28142823. c) Raynaud, J.; Absalon, C.; Gnanou, Y.; Taton, D. J. Am.
Chem. Soc. 2009, 131, 32013209.
Poster 18
The Roles of Au-F and Au-Au Interactions in Homogeneous Gold Catalysis

Neal P. Mankad, F. Dean Toste*
University of California at Berkeley
e-mail: fdtoste@berkeley.edu
Traditionally, homogeneous Au catalysis has consisted predominantly of

redox-neutral, Lewis acidic mechanisms. Recently, however, a new generation of
Au-catalyzed two-electron redox cycles allowing for cross-coupling transformations has
been discovered. These reactions often utilize the electrophilic fluorinating agent,
Selectfluor, as a sacrificial oxidant, indicating a special role for gold(III) fluoride
intermediates in these processes. Additionally, a significant dependence of catalytic
efficiency on Au-Au distance has been reported in several cases, indicating a special
role for gold-gold interactions during catalysis. In order to gain insight into these
phenomena, reactivity studies and physical measurements have been carried out on rare
examples of gold(III) fluoride complexes as well as several complexes with Au-Au
interactions. On the basis of these studies, conclusions on the important roles of Au-F
and Au-Au interactions in Au-catalyzed two-electron redox cycles will be presented.
Based on these studies, a new generation of catalysts has been designed that allows for
more efficient catalysis and careful mechanistic analysis. Preliminary results with these
new catalysts also will be presented.
Poster 19
Selective and Multiple Functionalization of N-Heterocycles and Benzylic

Cross-Coupling of Quinolines via Mg- and Zn-Organometallic Intermediates
Sophia M. Manolikakes, Milica Jaric, Andreas K. Steib, Stphanie Duez, Paul Knochel*
Ludwig-Maximilians-Universitt Mnchen, Department Chemie, Butenandtstr. 5-13, Haus F, 81377
Mnchen, Germany
e-mail: sophia.manolikakes@cup.uni-muenchen.de
Recently our group has demonstrated that the metalation of pyridine and quinoline
can be achieved by the use TMPMgClLiCl (TMP = 2,2,6,6-tetramethylpiperidyl) in the
presence of the lewis acid BF3OEt2.[1] This metalation protocol can also be applied to
more complex N-heterocycles such as quinine and nicotine. The resulting
Mg-compounds react with various electrophiles and also undergo transition
metal-catalyzed cross-coupling reactions.[2] In the case of quinine the procedure can be
modified in such a way, that it is possible to switch from position 3 of the quinoline
scaffold to position 2. Besides TMPMgClLiCl, the milder base
[3]
TMP2ZnMgCl22LiCl may be applied for a successive metalation of the pyridine
scaffold allowing a full ring functionalization. The even more sensitive base
TMPZnClLiCl[ 4 ] allows to perform a benzylic metalation of methyl substituted
quinolines and isoquinolines. Subsequent Pd(OAc)2- catalyzed arylation, in the presence
of an adequate Phos-ligand, proceeds well with various aryl bromides.
[1] Jaric, M.; Haag, B.A.; Unsinn, A; Karaghiosoff, K.; Knochel, P. Angew. Chem. Int
Ed. 2010, 49, 5454-5455.
[2] Jaric, M.; Haag, B.A.; Manolikakes, S.M.; Knochel, P. Org. Lett. 2011, 13,
2309-2309.
[3] Wunderlich, S.H.; Knochel, P. Angew. Chem. Int Ed. 2007, 46, 7685-7688.
[4] Mosrin, M.; Knochel, P. Org. Lett. 2009, 11, 1837-1840.
Poster 20
Easy access to saturated abnormal NHC-gold(I) complexes

Rubn Manzano,a Dominic Riedel,b A. Stephen K. Hashmia,b*
a
Catalysis Research Laboratory, Im Neuenheimer Feld 584, 69120 Heidelberg, Germany;
b
Organisch-Chemisches Institut, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
e-mail: hashmi@hashmi.de
N-Heterocyclic carbenes (NHCs) are now one of the most popular class of ligands in
organometallic chemistry. This probably is based on the high reactivity and exceptional
stability of the corresponding catalysts.[1] However, NHCs usually bind metals through
the C2 position of the heterocycle, and the rare cases of abnormal binding (i.e., through
C4 or C5) usually involve blocking the C2 position. After reporting the synthesis of
NHC complexes from gold coordinated isonitrile compounds,[2] we report here the
straightforward synthesis of saturated abnormal carbene gold (I) complexes. The
synthesis is based on a [3+2] cycloaddition of azomethine ylides and isonitrile gold (I)
complexes, and tolerates a wide variety of substituents on the nitrogen atoms, including
aliphatic, aromatic and heteroaromatic groups. X-ray diffraction analysis
unambiguously confirms the first saturated abnormal carbene structure.
[1] a) Kcher, C. K.; Hermann, W. A. Angew. Chem. Int. Ed. 1997, 36, 2162-2187; b)
Hahn, F. E.; Jahnke, M. C. Angew. Chem. Int. Ed. 2008, 47, 3122-3172.
[2] a) Hashmi, A. S. K.; Lothschtz, C.; Bhling, C.; Hengst, T.; Hubbert, C.;
Rominger, F. Adv. Synth. Catal. 2010, 352, 3001-3012; b) A. S. K. Hashmi, C.
Lothschtz, K. Graf, T. Hffner, A. Schuster, F. Rominger Adv. Synth. Catal. 2011,
353, 14071412
Poster 21
Diamination of internal alkenes

Martnez Claudio,a Muiz Kiliana,b*
a
Institute of Chemical Research of Catalonia (ICIQ), Spain; bCatalan Institution for Research and
Advanced Studies (ICREA), Spain
e-mail: cmartinez@iciq.es, kmuniz@iciq.es
We have recently been interested in the application of palladium catalysts to realise

unprecedented diamination reactions of internal alkenes.[1]-[3] Within this context, the
application of suitable high oxidation state palladium catalysis represents the key
methodology. We now report the first protocol for palladium catalysed intermolecular
diamination reactions of internal alkenes, which employ readily available nitrogen
sources. The diamination products are formed with complete regioselectivity and
chemoselectivity.[4]
Intermolecular diamination of internal alkenes:
HNTos2
Palladium- NTos2
Catalyst
R R
Iodo(III) N
Oxidant O
O
H
O N O
Diamination Product
[1] Muiz, K.; Hvelmann, C. H.; Streuff, J. J. Am. Chem. Soc. 2008, 130, 763.
[2] Streuff, J.; Hvelmann, C. H.; Nieger, M.; Muiz, K. J. Am. Chem. Soc. 2005, 125,
14586.
[3] Muiz, K. J. Am. Chem. Soc. 2007, 129, 14542.
[4] Martnez, C.; Muiz, K. manuscript in preparation.
Poster 22
Dioxocin nitrogen derivates: novel ligands for dinuclear complexes

Martnez-Ferrat Oriol,a Josep Maria Lpez-Valbuena,a George J. P. Britovsek,b*
Carmen Claver,c* Piet W. N. M. van Leeuwena*
a
Institute of Chemical Research of Catalonia (ICIQ), bDepartment of Chemistry, Imperial College London,
c
Departament de Qumica Fsica i Inorgnica, Universitat Rovira i Virgili
e-mail: omartinez@iciq.es
Diiron centers are the active site for some enzymes such as hemerythrin, methane
monooxygenase, flavo-diiron proteins etc.[ 1 ] Dioxocin phosphorus derivates
demonstrated their ability to form rhodium dinuclear complexes.[ 2 ] The nitrogen
derivatives were developed in view of the advantages of nitrogen ligands, namely their
chemical robustness, their stabilization of high oxidation state transition-metal species,
and their affinity towards metals from the first period such as Fe and Cu.
In this communication we present the synthesis of dioxocin tetranitrogen derivatives.
The bromodioxocin was aminated via an Ullman coupling reaction with ammonia.
Further condensations with different pyridinocarboxaldehydes led to the formation of
the new ligands. Dinuclear Fe complexes were formed with the use of these ligands.
Several catalytic reactions are being studied. such as epoxidation and phenol coupling.
[1] a) Wallar, B. J.; Lipscomb, J. D. Chem. Rer. 1996, 96, 2625-2657; b) Solomon, E.
I.; Brunold, T. C.; Davis, M. I.; Kemsley, J. N.; Lee, S.-K.; Lehnert, N.; Neese, F.;
Skulan, A. J.; Yang, Y.-S.; Zhou, J. Chem. Rev. 2000, 100, 235-349. c) Friedle, S.;
Reisner, E.; Lippard, S. J.; Chem. Soc. Rev., 2010, 39, 27682779
[2] Lpez-Valbuena, J. M.; Escudero-Adan, E. C.; Benet-Buchholz, J.; Freixa, Z.; van
Leeuwen, P. W. N M. Dalton Trans. 2010, 39, 8560-8574
Poster 23
Synthesis of Phospholes by 1,1-Carboboration Reaction

Juri Mbus, Roland Frhlich, Gerald Kehr, Gerhard Erker*
Organisch-chemisches Institut, WWU Mnster, Corrensstrae 40, 48149 Mnster
e-mail: ju.ri@uni-muenster.de
Bis(alkynyl)phosphanes were found to undergo clean reaction with B(C6F5)3 to yield

highly substituted 3-boryl-phospholes at reaction temperatures between 50 C and
80 C within hours. The boryl moiety was shown to undergo Suzuki-Miyaura-type cross
coupling reactions with different aryl halides to form the 3-aryl phospholes in up to 77%
yield.[1]
R
R R
B(C6 F5)3 B(C6F5)2 Ph
Ph-I
Ar P Ar P Ar P
C6F5 (Pd0) C6F5
R base R
R
Ar = Tipp, Mes
R = TMS, nPr, Ph
The mechanism of the transformation involves a sequence of two 1,1-carboboration

reactions. The reactions proceed by migration of the phosphanyl substituent via the
formation of a zwitterionic phosphirenium borate species.
[1] Mbus, J.; Bonnin, Q.; Ueda K.; Frhlich R.; Itami K; Kehr G.; Erker G. Angew.
Chem. Int. Ed. 2012, 53, DOI: 10.1002/anie.201107398.
Poster 24
Metal-Driven Preorganization in Organocatalysis

Tathagata Mukherjee, John A.Gladysz*
Texas A&M University, College Station, TX, USA
e-mail: gladysz@mail.chem.tamu.edu
The concept of preorganization involves engineering a receptor to be complementary

to a guest prior to a binding event. This can render the host-guest interaction
entropically and enthalpically more favorable. This notion can be extended further to
chiral hydrogen bond donors as they are immensely popular in enantioselective
organocatalysis.
EtOOC COOEt
NO2 COOEt 10 mol% catalyst
+ NO2
CH2Cl2, rt
COOEt
4 days
PF6 GBI HN
Ru NH catalyst: RuGBI
OC N NH N
N NH N 93%, 96% (ee) 54%, 55% (ee)
NH
NH N
N RuGBI H GBI
H
To put to test the effect of "metal-driven preorganization in organocatalysis" we have

chosen a 2-guanidinobenzimidazole derivative (GBI) as a simple hydrogen bond donor.
GBI is an effective ligand, and upon complexation to transition or main group metals it
becomes preorganized for several hydrogen bonding motifs as rotational degrees of
freedom that are intrinsic to the ligand are greatly reduced. Upon preorganization both
the reactivity and enantioselectivity are enhanced significantly.
Poster 25
Pd-Catalyzed CH Arylation and Alkylation Using Radicals Generated Under

Mild Conditions
Sharon R. Neufeldt, Dipannita Kalyani, Kate B. McMurtrey, Melanie S. Sanford*
University of Michigan, Ann Arbor, MI, USA
e-mail: mssanfor@umich.com
Palladium catalysis has been widely successful as a means to convert C-H bonds to
CC bonds. Nevertheless, functionalization of unactivated C-H sites typically requires
high temperatures, which can render these systems prohibitively harsh. Previous
mechanistic studies on Pd-catalyzed C-H arylations from our group have suggested that
the use of more kinetically reactive oxidants could permit lower reaction
temperatures.[1] We reasoned that carbon-centered radicals, generated under mild
conditions, might be more kinetically reactive alternatives to other common arylating
oxidants. To this end, we have developed a room-temperature Pd-catalyzed C-H
arylation that utilizes carbon radicals generated from aryldiazonium salts by
visible-light photoredox catalysis.[2] We have further discovered that diaryliodonium
salts, which are known to effect Pd-catalyzed CH arylation under thermal conditions
(100 C), can also operate under a Pd/photoredox manifold at room temperature. In
addition, we are investigating the use of organoboron compounds as precursors to
carbon-centered radicals for Pd-catalyzed C-H arylation and alkylation reactions.
[1] Deprez, N. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 1123411241.
[2] Kalyani, D.; McMurtrey, K. B.; Neufeldt, S. R.; Sanford, M. S. J. Am. Chem. Soc.
2011, 133, 1856618569.
Poster 26
Limits of Activity: Weakly Coordinating Ligands in Arylphosphinesulfonato Pd(II)

Polymerization Catalysts
Boris Neuwald, Franz lscher, Ingo Gttker-Schnetmann, Stefan Mecking*
Chair of Chemical Materials Science, Department of Chemistry, University of Konstanz, Germany
e-mail: Stefan.Mecking@uni-konstanz.de
Catalytic insertion polymerization of ethylene and propylene is employed on a vast

scale. By contrast, an insertion polymerization of electron deficient polar substituted
vinyl monomers has remained elusive. Phosphinesulfonato Pd(II)complexes
[(PÔ)PdMe(L)] are versatile precursors for the copolymerization of ethylene with
polar monomers towards linear polymers and the past years have witnessed a
remarkable advance of the scope of monomers amenable to insertion
copolymerization.[1] The reactivity of well-defined single-component catalyst precursors
[(PÔ)PdMe(L)] (1-L) towards acrylates depends crucially on the coordination strength
of the ligand L. Highly reactive precursors with L = dmso for the first time enabled
consecutive insertions to high-acrylate content ethylene copolymers, as well as
homooligomerization of acrylates.[2] Detailed studies on the influence of the ligand L
revealed that the (PÔ)PdMe fragment exhibits an intrinsic limitation with respect to
coordination of weak donors, due to bridging coordination of the (PÔ)-ligand. The in
situ generated ligand L free species 1 has been identified in homo- and
copolymerization experiments as the most active possible catalyst.
[1] a) Drent, E.; v. Dijk, R.; v. Ginkel, R.; v. Oort, B.; Pugh, R. I. Chem. Commun. 2002,
744-745; b) Nakamura, A; Ito, S.; Nozaki, K. Chem. Rev. 2009, 109, 5215-5244.
[2] Guironnet, D.; Roesle, P.; Rnzi, T.; Gttker-Schnetmann, I;. Mecking, S. J. Am.
Chem. Soc. 2009, 131, 422-423.
Poster 27
Gold(I)-Catalyzed [2+2+2] Cycloaddition of Alkynes with Ketoalkenes

Carla Obradors, Antonio M. Echavarren *
Institute of Chemical Research of Catalonia (ICIQ)
aechavarren@iciq.es
Gold has emerged as an exceptional catalyst for a variety of complex organic

transformations through the selective activation of alkynes, allenes and alkenes.[1] An
interesting example that leads to elaborated molecular skeletons involves the
cycloisomerization of enynes bearing a carbonyl group at the alkenyl chain.[2] We have
now developed a new intermolecular version of this reaction for the synthesis of
[3.2.1]-oxabicycles from alkynes and ketoalkenes using gold(I) complexes bearing
bulky 1,1-biphenyl-2-dialkylphoshines as catalysts.
Ar tBu
R1 O M
e
R1 tBu
O LAu+ (3 mol%) P iPr
Ar +O1 A(33mo
lC
% )
(3mol%) 1O
RAr O R3
A
r +R R DCE, 50 C O L=
R2 M
e C D
C
HE
Cl,0.5M,80
C 2 iPr
O 22 O R
M
e 15 examples
(5
:1
) M
e iPr
42-99%
The scope of this process as well as theoretical studies to determine the reaction
mechanism will be presented.
[1] Gorin, D. J.; Sherry, B. D.; Toste, F. D. Nature 2007, 446, 395. Jimnez-Nez, E.;
Echavarren, A. M. Chem. Rev. 2007, 107, 333. Rudolph, M.; Hashmi, A. S. K.
Chem. Commun. 2011, 47, 6536.
[2] Jimnez-Nez, E.; Claverie, C. K.; Nieto-Oberhuber, C.; Echavarren, A. M. Angew.
Chem. Int. Ed. 2006, 45, 5452. Huguet, N.; Echavarren, A. M. Synlett 2012, 23, 49.
Schelwies, M.; Dempwolff, A. L.; Rominger, F.; Helmchen, G. Angew. Chem. Int.
Ed. 2007, 46, 5598.
Poster 28
Hydroamination of Ethylene Catalyzed by Novel Platinum(II) N-Heterocyclic

Carbene Complexes
Jos Cabrera, Robin Padilla,a Michael Limbacha,b*
a
a
Catalysis Research Laboratory (CaRLa) Im Neuenheimer Feld 584, 69120 Heidelberg, Germany;
b
BASF SE, Synthesis and Homogeneous Catalysis, GCS/C M313, Carl Bosch Strae 38, 67056
Ludwigshafen, Germany
e-mail: Michael.limbach@basf.com
The direct amination of unactivated alkenes is of particular industrial interest as

nitrogen functionalities are widely found in both bulk and fine chemical products.[1] We
have previously reported the preparation of novel Pt(II) CNC pincer complexes and
their application in a hydrovinylation reaction.[2] In our most recent work,[3] related
Pt(II) complexes containing CN- and CNC- based NHC pincer ligands were found to be
active in the hydroamination of ethylene with a wide range of amides. The resulting N-
ethyl amides are produced in good yields and mostly with Markovnikov selectivity.
Additionally, the presence of water increased the reactivity of the Pt(II) complexes
derived from bidentate ligands.
[1] Brown, E. G. Ring Nitrogen and Key Biomolecules; Springer: Boston, MA, 1998.
[2] D. Serra, P. Cao, J. Cabrera, R. Padilla, F. Rominger, M. Limbach, Organometallics
2011, 30, 1885-1895.
[3] P. Cao, J. Cabrera, R. Padilla, D. Serra, F. Rominger, M. Limbach, Organometallics
2012, 31, 921-929.
Poster 29
Intermediates in Iridium-Catalysed Imine Hydrogenation

York Schramm, Fabiola Barrios-Landeros, Andreas Pfaltz*
University of Basel, Department of Organic Chemistry, St. Johannsring 19, 4056 Basel, Switzerland
e-mail: york.schramm@unibas.ch
Hydrogenation of acetophenone- and benzophenone-based N-aryl-imines with

iridium complexes of bidentate P,N-Ligands like A has shown to provide very high
enantioselectivities along with full conversion to the corresponding amines.
Acyclic aliphatic N-aryl-imines however still remain challenging substrates with
such catalysts as often poor conversion and low enantioselectivites are observed (Figure
1).[1],[2],[3]
BArF
O
Ph2P N N N
Ir N
N N
A
100% conv. 30% conv. 100% conv. 70% conv. 100% conv.
89% ee 9% ee 20% ee 0% ee 17% ee
CH2Cl2, 23C,
1-100 bar H2, 4-24 h
Figure 1: asymmetric hydrogenation of aryl/alkylketone-derived imines.[1]
We identified new iridium complexes that were formed under reactions conditions.
These complexes were used as catalysts in asymmetric hydrogenation of acyclic
aliphatic imines and displayed enhanced enantioselectivity along with significantly
increased reactivity. Additional mechanistic investigations by X-Ray crystallography
and NMR spectroscopic experiments provided a better understanding of the reaction
course.
[1] P. Schnider, G. Koch, R. Prtt, A. Pfaltz, Chem. Eur. J. 1997, 3, 887

[2] A. Baeza, A. Pfaltz, Chem. Eur. J. 2010, 16, 4003
[3] T. C. Nugent, M. El-Shazly, Adv. Synth. Cat., 2010, 352, 753
Poster 30
Josiphos-type ligands bearing a stereogenic P-CF3 moiety and their application in

asymmetric hydrogenations
Rino Schwenk, Antonio Togni*
Department of Chemistry and Applied Biosciences, ETH Zrich, CH-8093 Zrich Switzerland
e-mail: schwenk@inorg.chem.ethz.ch
Trifluoromethyl substituents exhibit interesting electronic properties as well as little

steric demand. Josiphos,[1] as a very successful ligand in a broad range of
asymmetrically catalyzed reactions,[2] was chosen as backbone for studies on partially
electron poor analogues bearing a stereogenic P-CF3 moiety.
The asymmetric hydrogenation of imines applying the corresponding iridium(I)
complexes highlighted that a stereogenic phosphorus atom as ligand atom may not only
influence the outcome of a reaction.[3] In our case, the stereogenic phosphorus atom
vastly controls the sense of chiral induction.
[1] Togni, A. and coworkers, J. Am. Chem. Soc. 1994, 116, 4062-4066.
[2] For review, see e.g. Barbaro, P. et al., Coord. Chem. Rev. 2004, 248, 2131-2150.
[3] Chen, W. P. et al., J. Am. Chem. Soc. 2006, 128, 3922-3923.
Poster 31
Mechanistic Studies on the Iridium Catalyzed Hydroamination of Strained and

Unstrained Aliphatic Alkenes
Christo S. Sevov, John F. Hartwig*
University of California Berkeley
e-mail: jhartwig@berkeley.edu
The intermolecular asymmetric hydroamination of unactivated alkenes remains an

unsolved challenge. Iridium complexes of chiral nonracemic bisphosphines were shown
to catalyze the hydroamination of norbornene with aryl- and tosyl- amides to produce
products in high yields and high enantiomeric excess (ee). The more challenging
hydroamination of terminal aliphatic alkenes proceeds with high conversion but poor
enantioselectivity. Mechanisms for the iridium-catalyzed hydroamination of bicyclic
and terminal alkenes were proposed after kinetic data for the catalytic reaction were
gathered and catalytic intermediates were characterized. The resting state species was
characterized in the solid and solution state as an iridium(amido)amidate complex that
forms following oxidative addition of an N-H bond. From the resting state, reversible
dissociation of the amido ligand forms a 2 bound amidate iridium complex. Catalyst
reorganization, possibly formation of the 1 iridium amidate from the 2 iridium
amidate, is the turnover limiting step (TLS) for the hydroamination of norbornene. The
less activated aliphatic alkenes follow a first order rate dependence on the concentration
of alkene, which implies that insertion or reductive elimination is the TLS. Deuterium
labeling experiments provide evidence for an off-cycle -hydride elimination step
followed by unselective enamine hydrogenation that generates amine products with low
ee.
Poster 32
Expanding the Scope of Selective Alkene Oligomerisation

Tom E. Stennett, Duncan F. Wass*
School of Chemistry, University of Bristol, Cantocks Close, Bristol, BS8 1TS, UK
e-mail: chtes@bristol.ac.uk
Selective tri- and tetramerisation of ethylene provides an efficient route to 1-hexene

and 1-octene, whereas isoprene can also be trimerised to yield desirable terpenes.
Current benchmark oligomerisation catalysts.[1]-[3] require large quantities of an
aluminoxane activator, and our aim is to reduce or eliminate this requirement by
investigating alternative activation methods. An ionic chromium (III) species,
[CrCl2(THF)4][Al(OC4F9)4] (A), has been synthesised and characterised. When
combined with diphosphine ligands and 10 equivalents of AlMe3, A yields a species
active for the selective oligomerisation of ethylene. Catalyst productivities of up to
2.5x104 g gCr-1 h-1 were observed, while the excellent selectivities to 1-hexene and
1-octene from the original MAO-activated system[1]-[3] were retained.
[CrCl2(THF)4][Al(OC4F9)4] Isolation of potentially catalytically
3
"PNP" ligand
relevant bis-chelate Cr complexes
2.5 x 104 g(gCr h)-1
10 AlMe3, PhCl 95% selectivity during these investigations led us to
consider a class of molybdenum complexes as model compounds. A series of known (B)
and novel (C-E) complexes of the form [Mo(N2)2(diphos)2] (diphos = dppe (B),[4]
Ph2PN(i-Pr)PPh2 (C), Ph2PN(Me)PPh2 (D) o-(PPh2)2C6H4 (E)) has been synthesised
and the compounds reactivity towards the alkenes used in selective oligomerisation
investigated.
[1] Carter, A.; Cohen, S.A; Cooley, A.; Murphy, A.; Scutt, J., Wass, D.F.; Chem.
Commun. 2002, 858.
[2] Wass, D.F., BP Chemicals Ltd., WO, 02/04119, 2002.
[3] Bollmann, A.; Blann, K.; Dixon, J.T.; Hess, F.M.; Killian, E.; Maumela, H.;
McGuinness, D.S.; Morgan, D.H.; Nevelling, A.; Otto, S.; Overett, M.; Slawin,
A.M.Z.; Wasserscheid, P.; Kuhlmann, S.; J. Am. Chem. Soc., 2004, 126, 14712
[4] Byrne, J.W.; Blaser, H.U.; Osborn, J.A.; J. Am. Chem. Soc., 1975, 97(13), 3871
Poster 33
Rhodium-Catalysed Hydroformylation of 1,3-Butadiene to Adipic Aldehyde

Eszter Takcs,a Sebastian Schmidt,b Stuart Smith,a Peter Hofmanna,b*
a
Catalysis Research Laboratory CaRLa, Im Neuenheimer Feld 584, 69120 Heidelberg, Germany;
b
Institute of Organic Chemistry, University of Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg,
Germany
e-mail: ph@oci.uni-heidelberg.de
The rhodium-catalysed bis-hydroformylation of 1,3-butadiene has been investigated

both theoretically and experimentally. DFT calculations on the reaction mechanism
performed for a novel family of highly n-selective chelating bidentate phosphite ligands
predict that in the first hydroformylation step the branched (iso) addition of a rhodium
hydride intermediate to 1,3-butadiene is slightly preferred over the normal (n) addition
and forms stabile 3-methallyl complexes.[1]
The hydroformylation of these intermediates produces (E/Z)-3-pentenals and further
products originating from them. Experimental studies have confirmed that for most
ligands this is the dominant reaction pathway; however, the formation of 4-pentenal and
1,6-hexanedial (adipic aldehyde) were also observed. These products result from the
normal (n) addition of a rhodium hydride to 1,3-butadiene.[2]
In this part of the research we focus our attention upon the design, synthesis and
catalyst screening of new bisphosphite ligands and investigate their suitability as
potential ligands in the double hydroformylation reaction of 1,3-butadiene to adipic
aldehyde.
[1] Schmidt, S. Diploma Thesis, University of Heidelberg 2010.

[2] Smith, S.; Rosendahl, T.; Hofmann, P. Organometallics 2011, 30, 3643.
Poster 34
Asymmetric nanocatalysis using N-heterocyclic carbenes

as chiral modifiers
Ranganath V. S. Kalluri, Dan-Tam D. Tang, Frank Glorius*
Organisch-Chemisches Institut der Westflischen Wilhelms-Universitt Mnster, Corrensstrae 40,
48149 Mnster, Germany
e-mail: glorius@uni-muenster.de
Various heterogeneous asymmetric catalytic systems have been successfully

developed to overcome problems in homogeneous medium.[1] The activity of a
heterogeneous catalyst is dependent on the structure and composition of its surface,
which can be both change by variation of the environment.[2] Nanoparticles (NPs) are
considered as semi-heterogeneous support since they are readily dispersed in the
reaction medium.[3] Although using N-heterocyclic carbenes (NHCs) as ligands has had
a tremendous impact on organometallic chemistry in the last years, chiral NHCs have
not been explored as chiral modifiers on the surface of NPs to generate a novel
heterogeneous catalytic system.[4] Herein, we report the preparation of Pd NPs on the
surface of Fe3O4 NPs stabilized by chiral NHCs.[5] The catalytic properties of these
surface modified Pd/Fe3O4 NPs which could be magnetically recovered and recycled
were evaluated in the -arylation of ketones exhibiting interesting ees. The details of
this reaction and will be discussed and the influence of the modifier will be investigated.
[1] Heitbaum, M; Glorius, F.; Escher, I. Angew. Chem. Int. Ed. 2006, 45, 4732-4762.
[2] Tao, F.; Grass, M. E.; Zhang, Y.; Butcher, D. R., Renzas, J. R.; Liu, Z.; Chung, J. Y.;
Mun, B. S.; Salmeron, M.; Somarjai, G. A. Science 2008, 322, 932-934.
[3] Astruc, D.; Lu, F.; Aranzaes, J. R. Angew. Chem. Int. Ed. 2005, 44, 7852-7872.
[4] Glorius, F. NHCs in Transition Metal Catalysis, Ed.; Springer: Berlin, 2007.
[5] Ranganath, K.; Kloesges, J.; Schfer, A.; Glorius, F. Angew. Chem. Int. Ed. 2010, 49,
7786-7789.
Poster 35
Pd-Catalyzed Synthesis of ArSCF3 Compounds Under Mild Conditions

Georgiy Teverovskiy, David S. Surry, S. L. Buchwald*
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge,
MA 02139
e-mail: sbuchwal@mit.edu
Aryl trifluoromethyl sulfides (ArSCF3) are an important class of compounds in both

the pharmaceutical and agrochemical areas owing to the capacity of SCF3 to act as a
lipophilic electron-withdrawing group. Access to these compounds, however, is
complicated by a lack of efficient, safe and general methods. Recent reports from our
group regarding novel ligands such as BrettPhos and its analogs have allowed for the
successful coupling of weak nucleophiles traditionally thought to be reluctant
participants in a typical Pd(0)/(II) catalytic cycle. In light of this, we hypothesized that a
similar system might allow for the formation of an aromatic CSCF3 bond. By using the
air and moisture stable AgSCF3 reagent and Ph(Et)3NI in the presence of catalytic
amounts of Pd(0)/BrettPhos, we were able to convert a wide range of aryl and
heteroaryl bromides into their corresponding aryl trifluoromethyl sulfides under mild
conditions and in good to excellent yield. Furthermore, we were able to apply this
methodology toward the formal synthesis of Toltrazuril.[1]
[1] Teverovskiy, G.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50,
7312-7314.
Poster 36
Catalytic Asymmetric Fischer Indolization

Matthew J. Webber, Steffen Mller, Benjamin List*
Max-Planck-Institut fr Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mlheim an der Ruhr,
Germany
e-mail: list@kofo.mpg.de
Since its discovery almost 130 years ago, the Fischer indolization of phenyl
hydrazones has been extensively studied and has consistently proved to be among the
most widely used methods for the synthesis of indoles.[1] Despite this interest, no
catalytic asymmetric variant had been reported to date. Here we report the first such
example, giving access to 3-substituted tetrahydrocarbazoles in high yields and
enantioselectivities. Crucial to the method is the removal of the catalyst-poisoning
ammonia by-product by an ion exchange resin.[2]
Subsequent studies have shown the method to be applicable to the modular,

enantioselective synthesis of polyaromatic indoles exhibiting helical chirality.
[1] Fischer, E.; Jourdan, F. Ber. Dtsch. Chem. Ges. 1883, 16, 2241.
[2] Mller, S.; Webber, M. J.; List, B. J. Am. Chem. Soc. 2011, 133, 18534-18537.
Poster 37
Mechanistic Insights into Amidopalladation and Development of New Aerobic

Aza-Wacker Palladium Catalysts Utilizing Bidentate Nitrogen Ligands
Paul B. White, Shannon S. Stahl*
Department of Chemistry, University of Wisconsin-Madison
e-mail: stahl@chem.wisc.edu
In recent years, the Stahl group has reported a number of different reactions for
oxidative amidation capable of using molecular oxygen as the stoichiometric oxidant.[1]
Amidopalladation of the alkene leads to formation of a carbon-nitrogen bond and is a
key step in these catalytic reactions. We have previously obtained evidence that the
amidopalladation step proceeds via alkene insertion into a Pd-N bond.[2] This poster will
present a series of well-defined (bpy)Pd(II)-sulfonamidate complexes, which have been
prepared and shown to react via insertion of a tethered alkene to afford an
alkyl-palladium(II) species.[3] These stoichiometric alkene insertion reactions are found
to be reversible, and the alkyl-palladium(II) product of this equilibrium undergoes
beta-hydride elimination to generate oxidative amination products.
REVERSIBLE
These fundamental
SO Ar 3
Concentration (mM)
2
ALKENE INSERTION
SO Ar
N
2
k
N 2 SO Ar
N
A studies2.5
2
have
t
1 t 2 k
( Bu bpy)Pd ( Bu bpy)Pd
2
Cl -1 k
2
Cl
B
provided the basis
1.5
1
+ isomers
C 0.5
A t Bu t Bu B C for our
0
0 9
recent18 27 36 45
3
t Time (10 s)
Bu bpy =
2
N N pursuit of improved
catalyst systems for aerobic oxidative amidation reactions, employing a Pd(II) salt in
combination with an ancillary bidentate nitrogen ligand. Dramatically higher catalytic
activity has been observed with a Pd(OAc)2/4,5-diazafluoren-9-one catalyst system.
[1] a) Fix, S. R.; Brice, J. L.; Stahl, S. S. Angew. Chem. Int. Ed., 2002, 41, 164-166. b)
McDonald, R. I.; Stahl, S. S. Angew. Chem. Int. Ed., 2010, 49, 5529-5532. c)
McDonald, R. I.; White, P. B.; Weinstein, A. B.; Tam, C. P.; Stahl, S. S. Org. Lett.
2011, 13, 2830-2833.
[2] Liu, G.; Stahl, S. S. J. Am. Chem. Soc., 2007, 129, 6328-6335.
[3] White, P. B.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 18594-18597.
Poster 38
Iterative Asymmetric Hydroformylation-Wittig Olefination

Gene W. Wong, Clark R. Landis*
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI,
53706
e-mail: landis@chem.wisc.edu
One-pot asymmetric hydroformylation-Wittig olefinations (AHF-WO) yield

structurally diverse alkenes using rhodium-bis-3,4-diazaphospholane catalysts in the
presence of a Wittig ylide. The products, -chiral ,-unsaturated carbonyls, constitute
useful intermediates in total syntheses. Iterative AHF-WO sequences demonstrate the
synthesis of larger complex materials. For example, oligomeric polyesters result from
one-pot iterative tandem procedure with a single catalyst loading.
Poster 39
A Mechanistic Investigation of the Chromium-Mediated Bergman Cyclization

Kai E. O. Ylijoki,a Sverine Lavy,a Tho Berclaz,b E. Peter Kndiga*
Departments of Organica and Physicalb Chemistry, University of Geneva, 30 Quai Ernest Ansermet, 1211
Geneva 4, Switzerland
e-mail: peter.kundig@unige.ch
The Bergman cyclization of conjugated enediynes has generated significant interest

since the first reports.[1] OConnor has shown that complexation of an enediyne
substrate to a ruthenium or iron transition metal centre results in rapid
cycloaromatization at room temperature, yielding metal-arene -complexes.[2] With our
long-standing interest in the preparation and functionalization of early transition metal
arene complexes, we report that in the presence of (naphthalene)Cr(CO)3, enediyne
substrates readily cycloaromatize at room temperature. To probe the mechanism of this
novel process, we have undertaken a combined computational and spectroscopic study
to determine the substrate coordination mode and whether a biradical intermediate akin
to the thermal Bergman cyclization lies on the potential energy surface.
[1] a) Darby, N.; Kim, C. U.; Salan, J. A.; Shelton, K. W.; Takada, S.; Masamune, S.
Chem. Commun. 1971, 1516; b) Jones, R. B.; Bergman, R. G. J. Am. Chem. Soc.
1972, 94, 660.
[2] O'Connor, J. M.; Friese, S. J.; Rodgers, B. L. J. Am. Chem. Soc. 2005, 127, 16342.
Lecturer
Moshe Kol
Friedhelm Balkenhohl
School of Chemistry
BASF SE, Synthesis and Homogeneous
Tel Aviv University
Catalysis (GCS)
Tel Aviv 69978; Israel
Carl-Bosch-Strae 38,
moshekol@post.tau.ac.il
67056 Ludwigshafen, Germany
friedhelm.balkenhohl@basf.com
Kazushi Mashima
Department of Chemistry
Straub Bernd
Graduate School of Engineering Science
Universitt Heidelberg
Osaka University
Organisch-Chemisches Institut
Toyonaka, Osaka 560-8531, Japan
Im Neuenheimer Feld 270
mashima@chem.es.osaka-u.ac.jp
69120 Heidelberg, Germany
straub@oci.uni-heidelberg.de
Warren E. Piers
Christophe Copret
University of Calgary
2500 University Dr. NW
ETH Zrich / HCI H 229
Calgary, Alberta, CANADA T2N 1N4
Wolfgang-Pauli-Strae 10
wpiers@ucalgary.ca
8093 Zrich, Switzerland
ccoperet@inorg.chem.ethz.ch
Dieter Vogt
Eindhoven University of Technology
Klaus Ditrich
Department of Chemical Engineering and
BASF SE
Chemistry
Carl-Bosch-Strasse
Helix building, STW 4.34
GVF/B A030
P.O. Box 513 / Den Dolech 2
67056 Ludwigshafen, Germany
5600 MB Eindhoven; The Netherlands
klaus.ditrich@basf.com
d.vogt@tue.nl
Deryn E. Fogg
Christina M. White
Centre for Catalysis Research &
Innovation
University of Illinois
270 Roger Adams Laboratory
University of Ottawa
600 South Mathews Ave.
10 Marie Curie
Ottawa, ON Canada; K1N 6N5
white@scs.illinois.edu
dfogg@uottawa.ca
Gregory C. Fu
Massachusetts Institute of Technology
77 Massachusetts Avenue, Room 18-290
gcf@mit.edu
Participants
Alexander Arlt Moti Gargir

Max-Planck-Institut fr Kohlenforschung The Weizmann Institute of Science
Kaiser-Wilhelm-Platz 1 76100 Rehovot, Israel
45470 Mlheim an der Ruhr, Germany moti.gargir@weizmann.ac.il
arlt@kofo.mpg.de
Matthias Grabowski
Nicolas Armanino Technische Universitt Berlin
ETH Zrich Fakultt II, Institut fr Chemie
Laboratory of Organic Chemistry Strae des 17. Juni 135
HCI H335 10623 Berlin, Germany
Wolfgang-Pauli-Strasse 10 grabowski@chem.tu-berlin.de
8093 Zrich, Switzerland
nicolas.armanino@org.chem.ethz.ch A. Stephen K. Hashmi
Organisch-Chemisches Institut der
Marcel Brill Universitt Heidelberg
Organisch-Chemisches Institut der Im Neuenheimer Feld 270
Universitt Heidelberg 69120 Heidelberg, Germany
Im Neuenheimer Feld 270 hashmi@hashmi.de
brill@oci.uni-heidelberg.de Berit Heggen
Max-Planck-Institut fr Kohlenforschung
Jose Cabrera Kaiser-Wilhelm-Platz 1
Catalysis Research Laboratory (CaRLa) 45470 Mlheim an der Ruhr, Germany
Im Neuenheimer Feld 584 heggen@kofo.mpg.de
jose.cabrera@carla-hd.de Peter Hofmann
Organisch-Chemisches Institut der
Qing-Hai Deng Universitt Heidelberg
Organisch-Chemisches Institut der Lehrstuhl fr Organische Chemie III
Universitt Heidelberg Im Neuenheimer Feld 270
Im Neuenheimer Feld 270 69120 Heidelberg, Germany
69120 Heidelberg, Germany ph@uni-hd.de
qinghaideng@hotmail.com
Christoph Hubbert
Stephanie Dupuy Organisch-Chemisches Institut der
School of Chemistry Universitt Heidelberg
Purdie Building, North Haugh Im Neuenheimer Feld 270
University of St Andrews 69120 Heidelberg, Germany
St Andrews, KY16 9ST, UK chubbert@oci.uni-heidelberg.de
sd53@st-andrews.ac.uk
Reinhard Jira
Oriol Martinez Ferrate Kabastastrae 9
Institute of Chemical Research of 81243 Mnchen, Germany
Catalonia (ICIQ) rw.jira@t-online.de
Av. Pasos Catalans 16
43007 Tarragona, Spain
oriol.martinez.ferrate@gmail.com
Takeharu Kageyama Neal Mankad
Catalysis Research Laboratory (CaRLa) Department of Chemistry
Im Neuenheimer Feld 584 University of California
69120 Heidelberg, Germany 619 Latimer Hall
takeharu.kageyama@carla-hd.de Berkeley, CA, 94720-1460, USA
neal.mankad@berkeley.edu
Yanbiao Kang
Catalysis Research Laboratory (CaRLa) Sophia Manolikakes
Im Neuenheimer Feld 584 Department Chemie und Biochemie
69120 Heidelberg, Germany Ludwig-Maximilians-Universitt
yanbiao.kang@carla-hd.de Butenandtstrae 5-13
81377 Mnchen, Germany
Andreas Kapelski sophia.manolikakes@cup.uni-
Institut fr Anorganische Chemie muenchen.de
RWTH Aachen
52056 Aachen, Germany Ruben Manzano
andreas.kapelski@ac.rwth-aachen.de Catalysis Research Laboratory (CaRLa)
Tillmann Kleine 69120 Heidelberg, Germany
RWTH Aachen University ruben.manzano@carla-hd.de
Landoltweg 1
52056 Aachen, Germany Claudio Martnez
tillmann.kleine@oc.rwth-aachen.de Institute of Chemical Research of
Catalonia (ICIQ)
Christoph Kornhaa Av. Pasos Catalans 16
Georg-August-Universitt Gttingen 43007 Tarragona, Spain
Institut fr Organische und Biomolekulare cmartinez@ICIQ.es
Chemie
Tammannstrasse 2 Juri Mbus
37077 Gttingen, Germany Universitt Mnster
ckornha@gwdg.de Institut fr Organische Chemie
Corrensstr. 40
Michael Lejkowski 48149 Mnster, Germany
Catalysis Research Laboratory (CaRLa) j_moeb01@uni-muenster.de
69120 Heidelberg, Germany Tathagata Mukherjee
michael.lejkowski@carla-hd.de Department of Chemistry
Texas A&M University
Michael Limbach College Station, TX 77843-3255, USA
Carl-Bosch-Strasse 38 tathagata.mukherjee@chem.tamu.edu
GCS/C M313
67056 Ludwigshafen, Germany Sharon Neufeldt
michael.limbach@basf.com University of Michigan
Ronald Lindner 930 N. University
Catalysis Research Laboratory (CaRLa) Ann Arbor, MI 48109-1055, USA
Im Neuenheimer Feld 584 sharose@umich.edu
ronald.lindner@carla-hd.de
Boris Neuwald Christo Sevov
Universitt Konstanz Department of Chemistry
Fachbereich Chemie Box 58-6 CLSL A410
Universittsstr. 10 University of Illinois
78457 Konstanz, Germany 600 South Mathews Ave.
boris.neuwald@uni-konstanz.de Urbana, IL 61801, USA
csevov@berkeley.edu
Carla Obradors
Departamento de Qumica Orgnica Thomas Stennett
Facultad de Ciencias School of Chemistry
Universidad Autnoma de Madrid University of Bristol
Cantoblanco 28049-Madrid, Spain Bristol BS8 1TS, UK
cobradors@iciq.es chtes@bristol.ac.uk
Robin Padilla Eszter Tacakz

Catalysis Research Laboratory (CaRLa) Catalysis Research Laboratory (CaRLa)
Im Neuenheimer Feld 584 Im Neuenheimer Feld 584
69120 Heidelberg, Germany 69120 Heidelberg, Germany
robin.padilla@carla-hd.de eszter.takacs@carla-hd.de
Philipp Plessow Daniel Tang

Catalysis Research Laboratory (CaRLa) Westflische Wilhelms-Universitt
Im Neuenheimer Feld 584 Mnster
69120 Heidelberg, Germany Organisch-Chemisches Institut
philipp-nikolaus.plessow@basf.com Corrensstrasse 40
48149 Mnster, Germany
Manojkumar Poonoth danieltang@uni-muenster.de
Catalysis Research Laboratory (CaRLa)
Im Neuenheimer Feld 584 Georgiy Teverovskiy
69120 Heidelberg, Germany Massachusetts Institute of Technology
manojkumar.poonoth@carla-hd.de 77 Massachusetts Avenue
Cambridge, MA 02139, USA
York Schramm gtev@mit.edu
Universitt Basel
Organische Chemie Matthew Webber
St. Johanns-Ring 19 Max-Planck-Institut fr Kohlenforschung
4056 Basel, Switzerland Kaiser-Wilhelm-Platz 1
york.schramm@unibas.ch 45470 Mlheim an der Ruhr, Germany
webber@kofo.mpg.de
Rino Schwenk
ETH Zrich Alexander Wetzel
Laboratorium fr Anorganische Chemie Catalysis Research Laboratory (CaRLa)
HCI H239 Im Neuenheimer Feld 584
Wolfgang-Pauli-Str. 10 69120 Heidelberg, Germany
8093 Zrich, Switzerland alexander.wetzel@carla-hd.de
schwenk@inorg.chem.ethz.ch
Paul White
University of Wisconsin-Madison
1101 University Avenue
Madison, Wisconsin 53706-1396, USA
pwhite@chem.wisc.edu
Kristina Wilckens
kristina.wilckens@carla-hd.de
Gene Wong
University of Wisconsin-Madison
1101 University Avenue
Madison 53706 WI, USA
gwong@chem.wisc.edu
Xuan Ye
xuan.ye@carla-hd.de
Kai Ylijoki
Department of Organic Chemistry,
University of Geneva - Sciences II, 30,
quai Ernest-Ansermet, CH-1211 Geneva 4,
Switzerland
kai.ylijoki@unige.ch
Your way to the conference venue:
dai
Deutsch Amerikanisches Institut
Sofienstrasse 12
69115 Heidelberg
From Hotel Europischer Hof
Hotel
dai Europischer
Hof
From Exzellenzhotel
dai
Exzellenz-
hotel
Heidelberg
Lunch Break Opportunities
Restaurants / Cafs
1 Bismarckplatz
Bismarck Square, various small restaurants, offering international
cuisine e.g. Sushi, Chinese, Turkish, German
2 Petit Paris Caf-Bistro

Fahrtgasse 18, daily changing lunch offers from 4,50
3 Medocs, Caf and Restaurant

Sophienstrae 7b, weekly changing lunch menu with 5 dishes from
2 5,50
4 Exotica Natural Specialties (in Shopping- Arcade Carr)

Rohrbacherstrae 8, salads, tapas, wraps, vegetarian dishes,
1 freshly squeezed juices and exotic fruits
3
7 6 8 5 Tiger and Dragons Food Corner (in Shopping- Arcade Carr)

10 Poststrae 1, asian cuisine with various dishes, also to take away
6 Raja Rani, Indian and Tandoori Restaurant

9 Friedrichstrae 15, indian and tandoori dishes from 3 to 10 , also to
take away, approx. 7 min. from Bismarck Square
4 5
7 Chilis, Caf and Restaurant
11
Plck 93a, vwide choice of turkish dishes from 3 to 6 , approx. 7
min. from Bismarck Square, free WLAN
8 Essighaus, Restaurant
Plck 97, home- style cuisine with lunch menu from 6,00
9 Rossi, Caf and Restaurant

Rohrbacherstrae 4, daily special lunch offers in the ambience of a
traditional coffee house
Other points of interest
10 Bus- Stop, for excursion
11 DAI

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th

5 CaRLa Winter School

Michael Limbach Peter Hofmann

All Sessions take place in the German-American-Institute Heidelberg

until 16:00 Arrival and Coffee Break

16:30 Welcome Address Thomas Rausch

18:00 Light Dinner and Get-together

Sunday, 4th March

10:00 Coffee Break

10:15 Lecture: Activation of CO and CO2 with Decamethylscandocinium-hydridoborate

11:15 Coffee Break

11:30 Flash Poster Presentations

12:00 Lunch Break (free time)

14:30 Lecture: Sustainable and Atom-Efficient Catalytic Routes to Amines

15:45 Training Session: Ligand Control in Homogeneous Catalysis The Molecular

16:45 Coffee Break

17:00 Flash Poster Presentations

17:30 Poster Session including light dinner

Monday, 5th March

9:00 Lecture: The Ruthenium Chemistry of Olefin Metathesis

10:00 Coffee Break

10:15 Training Session: Sustainable Metathesis

11:15 Coffee Break

11:30 Flash Poster Presentations

12:00 Lunch Break (free time)

14:30 Lecture: Rational Ligand Design

15:30 Coffee Break

16:45 Coffee Break

17:00 Flash Poster Presentations

17:30 Poster Session including light dinner

Tuesday, 6th March

9:00 Lecture: Well-defined supported catalysts via the controlled functionalization of

10:00 Coffee Break

10:15 Training Session: Support effects in single-site catalysts: A molecular point of

11:15 Coffee Break

11:30 Flash Poster Presentations

12:00 Lunch Break (free time)

14:30 Lecture: Designing of Catalysts for Stereoregular Polymerization of Propylene

15:30 Coffee Break

16:45 Coffee Break

17:00 Flash Poster Presentations

17:30 Poster Session including light dinner

Wednesday, 7th March

9:00 Lecture: Zinc Cluster Catalyzed Transesterification and Oxazoline Synthesis

10:00 Coffee Break

11:15 Coffee Break

11:30 Flash Poster Presentations

12:00 Lunch Break (free time)

14:30 Training Session: Industrial Bioprocesses - Basic Principles

15:30 Coffee Break

16:45 Coffee Break

17:00 Flash Poster Presentations

17:30 Poster Session including light dinner

Thursday, 8th March

9:00 Lecture: Palladium- and Nickel-Catalyzed Cross-Coupling Reactions of Alkyl

10:00 Coffee Break

10:15 Training Session: Enantioselective Nucleophilic Catalysis

11:15 Coffee Break

11:30 Flash Poster Presentations

12:00 Lunch Break (free time)

14:30 Transfer to Ludwigshafen

15:00 Excursion of BASFs Main Site in Ludwigshafen

19:00 Winter School Dinner in Kulturbrauerei

9:00 Lecture: Adding Aliphatic CH Bond Oxidations to Synthesis