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A R T I C L E I N F O
Article history:
Received 20 December 2014
Received in revised form 6 June 2015
Accepted 6 June 2015
Available online 20 June 2015
Keywords:
Partial uorination
Electrochemistry
Organic compounds
Ionic liquids
A B S T R A C T
Ionic liquids due to their advantageous properties gain importance in many elds. This study aims to
overview the use of ionic liquids in the selective partial uorination of organic compounds through
electrochemical method. In addition to ionic liquid based uorination, the earlier approaches of
uorination through an electrochemical process have also been highlighted. The factors such as
electrode materials (Pt, Ni, and C), types of solvents (CH3CN, DMC, THF, DME, Sulfone, etc.) and type of
electrolytes (Et3N3HF, Et3NF3HF, pyHF, etc.) which affect the electrochemical uorination of organic
compounds have been reviewed. For electrode preparation, the carbon, platinum and nickel were
considered suitable materials to be used as an electrode. In CH3CN media, Et3N3HF and Et4NF3HF
showed better efciency during uorination of organic compounds. Solvent play an important role in
electrochemical uorination of organic compounds, with the change of solvent the percentage yield is
highly affected. Py-HF is a convenient solvent-supporting electrolyte medium with a reasonably good
conductivity. The electrolyte containing solvents have some side effects on electrochemical uorination
of organic compounds as observed in cyclic voltammetric analysis. Therefore electrochemical
uorination to organic compounds without the use of solvent gained more importance. The ionic
liquids have been reported for its dual properties, as solvent as well as a uorinating agent for organic
compounds in electrochemical processes. It has been concluded that solvents free electrochemical
uorination of organic compounds gives good results as compare to solvent based. Ionic liquids due to
more oxidative stability were noted to have considerable effect on the yield and selectivity of organic
compound uorination.
2015 The Korean Society of Industrial and Engineering Chemistry. Published by Elsevier B.V. All rights
reserved.
Contents
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Fluorination process . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Effect of electrode materials on uorination process . . . .
Effect of solvents on electrochemical process . . . . . . . . .
Effect of supporting electrolytes on uorination process.
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27
27
28
29
31
Abbreviations: DMC, dimethyl carbonate; THF, tetrahydrofuran; DME, dimethoxyethane; CV, cyclic voltammogram; ECF, electro chimerical uorination; ILs, ionic liquids;
PTFE-FFP, poly tetra uoro ethylene-fresh frozen plasma; HF, hydrouoric acid; ECb ECn, electrochemical; MCN, acetonitrile; Py-HF, pyridine-hydrouoric acid; DCM,
dichloromethane; ECPF, electrochemical per-uorination.
* Corresponding authors. Tel.: +86 10 64435452; fax: +86 10 64445917.
E-mail addresses: ziaulhaqkhan11@gmail.com (Z.U.H. Khan), chenym@mail.buct.edu.cn (Y. Chen), pywan@mail.buct.edu.cn (P. Wan).
http://dx.doi.org/10.1016/j.jiec.2015.06.007
1226-086X/ 2015 The Korean Society of Industrial and Engineering Chemistry. Published by Elsevier B.V. All rights reserved.
Z.U.H. Khan et al. / Journal of Industrial and Engineering Chemistry 31 (2015) 2638
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27
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31
32
33
33
33
34
37
38
38
Introduction
Fluorinated organic compounds have unique properties and
especially partially uorinated organic compounds play an
important role in preparation of novel medicine [13], in the
area of agriculture [4] and also in development of functionalized
materials [5]. About 4045% of agrochemicals contained uorine
element in their compositions. Electro chimerical Fluorination
(ECF) is one of the best tools in uorination of organic compounds
that involved the conversion of CH to CF bond. Usually three
methods are used in electrochemical partial uorination to
organic compounds [610]. Among these methods, electrochemical partial uorination is very attractive because uorine atoms
can be introduced into organic molecules in one step under safe
conditions [7,11] and results in different types of new uorinated
organic compounds [1214]. General synthesis normally results
in large quantities of both inorganic and organic by-products. The
ECF is attractive methods and it is more advanced as compare to
other general methods and not accompanied by by-products
synthesis. Electrochemistry, since 50 years made a signicant
contribution in the area of uorination of organic compounds with
the development and commercialization of the Simons Process
[15]. In most case uorination process is completed in many
different ways, in which the bond between CC breaks and
subsequently rearranged with high extent, but the yield is very
poor. Electrochemical process is very friendly and not a case in the
handling of uorine gas and in several cases also conserves the
molecule functionality [16]. The ECF of organic compounds, direct
as well as indirect methods have been used. Fuchigami and his
co-worker reported electrochemical uorination of organic
compounds to dithioketals 92, by indirect method using Et4NBr
in catalytic amount and Et3N3HF was used as mediator as
uorinating agent to corresponding mono ouro thio ether 93,
and get very good result without formation of other by products
(Scheme 1) [17]. Similar results were reported by other
researchers using direct methods [17]. Ionic liquids (ILs) are
molten salts having melting point below 100 8C and are
considered as green solvent due to their advantageous properties
[18]. Ionic liquids are considered one of the best solvent in organic
syntheses, electro organic syntheses, catalysis and for polymerization [1925]. This study highlights the facile route of
electrochemical uorination of organic compounds. The factors
such as the electrode materials, solvents, electrolytes and other
additives which affect the uorination process have been
highlighted. The venture of ionic liquid for its potential application in the uorination of organic compounds has been described
in detail.
Fluorination process
Electrochemical uorination (ECF) in a-HF is generally used for
the electrochemical uorination to organic compounds. Partial
electrochemical uorination to organic compounds is useful tools
for the synthesis of new organic compounds using Simon process
in technical and laboratory level [26]. Till now the mechanism of
partial electrochemical uorination of organic compound using
Simon process are employed. Several proposals about the possible
mechanism of this process were made during the years [26] but
neither one was conrmed experimentally. Simons process takes
place at the surface of the Ni anode, covered by a NiF/NiFz-lm.
That was proved by an independent experiment as follows: 1.45 g
of CH3SO2F was treated in a PTFE-FEP vessel with 16 g of
anhydrous HF, previously electrolyzed in the Simons type
electrolytic cell during 46 h.
28
Z.U.H. Khan et al. / Journal of Industrial and Engineering Chemistry 31 (2015) 2638
Scheme 2.
Scheme 3.
Z.U.H. Khan et al. / Journal of Industrial and Engineering Chemistry 31 (2015) 2638
Scheme 5.
29
DME [38,39], have also been used. Py-HF is a convenient solventsupporting electrolyte medium with a reasonably good conductivity. Hence, efforts were also made to use this medium for
selective electrochemical uorination [40]. Selective uorination
leading to the formation of heteroatom uorine bonds should also
be considered as a signicant development [41]. Solvent play
important role in electrochemical uorination of organic compounds, with the change of solvent the percentage yield is highly
affected. The yield will be twice when ethereal solvent, such THF,
DME, Dioxin, instead of MCN that are used as solvent (run 36, 10),
while DCM and DMC have no effect on the yield of products. The
effect has been studied in Table 1.
More than 10 years ago, Fuchigami and his co-worker achieved
independently anodic a-uorination of ethyl a-phenyl the acetate
(1) in Et3N3HF/MeCN [4244] (Scheme 6).
Table 1
Anodic mono uorination of alkyl phenyl suldes [40].
Run
1
2
3
4
5
6
7
8
9
10
No.
5a
5a
5a
5a
5a
5a
5a
5a
5b
5b
H
H
H
H
H
H
H
H
Me
Me
Solvent
MeCN
MeCN
THF
THF
DME
Dioxane
DMC
DMF
MeCN
THF
+1.6
6.3a
+3.3
6.3a
6.3a
6.3a
6.3a
+1.6
+1.8
+3.3
2.1
2.0
6.1
5.0
4.5
3.0
3.0
4.0
4.0
6.1
23 (6a)
20 (6a)
45 (6a)
52 (6a)
57(6a)
47 (6a)
22 (6a)
5 (6a)
18(6b)
45(6b)
45
62
b
32
25
21
24
6
b
b
(7a)
(7a)
(7a)
(7a)
(7a)
(7a)
(7a)
(7a)
Fig. 1. Cyclic voltammograms for the oxidation of 4 mM of C6H5SCH2COOCH3 on Pt in CH3CN (A) 0.1 M TBAP and (B) Et3N3HF at different scanning speeds (v) (mV). (a) 20, (b)
40, (c) 80, (d) 160, (e) 320, and (f) 640 [46].
Z.U.H. Khan et al. / Journal of Industrial and Engineering Chemistry 31 (2015) 2638
30
Table 2
Oxidation peak potentials and peak currents of suldes contains active methylene group PhSCH2R [47].
ipal (mA cm2)
No
Sub. no
Substrate [R]
Epal (V)
TBAP/CH3CN
Et3N3HF/CH3CN
TBAP/CH3CN
Et3N3HF/CH3CN
1
2
3
4
5
6
7
8
1a
2a
3a
4a
5a
6a
7a
8a
COOMe
COOC6H4-Cl-P
CONC6H4-Cl-P
COOC6H4-NO2-P
CONH2
CONHC6H4-NO2-P
CONHC6H5
COOC6H5
1.62
1.84
1.63
1.76
1.71
1.69
1.71
1.69
1.46
1.72
1.63
1.62
1.57
1.52
1.48
1.04
3.27
2.71
1.50
2.78
1.64
1.58
1.48
3.69
4.43
3.75
3.06
2.94
2.17
2.11
2.46
1.07
Ipal rst anodic peak current, Epal anodic peak potential, S.R. = 40 mV/s, Concentration = 10 mM.
Table 3
Selective electro uorination of suldes containing active methylene groups [26].
No
Sulde
1a
2a
3a
4a
5a
6a
7a
8a
1
2
3
4
5
6
7
8
a
Sub. no
COOMe
COOC6H4-Cl-P
COOC6H4-Cl-P
COOC6H4-NO2-P
CONH2
CONHC6H4-NO2-P
CONHC6H5
COOC6H5
3.80
5.10
5.20
5.00
4.70
5.10
5.80
7.00
Product yielda
Total yield
b+c
72
12
7
6
22
6
6
17
5
56
56
50
27
36
28
10
77
68
63
56
49
42
34
27b
Un reacted substrate
14
22
5
10
14
Table 4
Anodic uorination of ethyl a-(phenylthio) acetate in Et3N3HF ionic liquid with or without ultrasonication.
Yielda (%)
Current/density
2
Selectivity of 2 (%)
Run
Ultrasonication
mA cm
Total
1
2
3
4
5
6
7
8
No
Yes
No
No
Yes
No
Yes
Yes
2.5
2.5
5.0
10
10
25
25
50
79
90
54
33
85
3
65
65
8
0
21
24
4
3
8
15
86
90
75
57
89
6
73
79
Determine by
91
100
72
58
95
50
89
82
19
FNMR.
Scheme 7.
Z.U.H. Khan et al. / Journal of Industrial and Engineering Chemistry 31 (2015) 2638
31
Table 5
Effect of solvent in Et3N3HF on anodic uorination of organic compounds.
No
Substrate
Products yields %
MeCN
DME
DMC
DMF
1
2
3
PhSCH3a,b
(Ph)2C5
5NNH2
PhSCH2COORc
21
54
57
62
22
95
43
5
31
12
a
b
c
Main products
Reference
PhSCH2F
Ph2CHF
PhSCHFCOOR
[6]
[34]
[41]
Scheme 8.
Table 6
Effect of supporting electrolytes in CH3CN on anodic uorination of organic compounds.
No
Substrate
Products yields %
Et3N3HF
Et4NF3HF
Py-NHF
Main product
Reference
PhSCHCF3
PhSCHFCOOEt
[49]
[47]
1
2
PhSCH2CF3
PhSCH2COOEt
62
61
61
Ph.S
77
64
Trace
4
5
PhSCH2COOR
54
56
37
72
73
[50]
80
66
[50]
[52]
PhSCHCOOR
[51]
[50]
Z.U.H. Khan et al. / Journal of Industrial and Engineering Chemistry 31 (2015) 2638
32
Table 7
Solvent effect on anodic uorination of 3-phenylthiophthalide [44].
Run
Reaction
Supporting electrolyte
1
2
3
4
5
6
7
MeCN
DMC
THF
DME
[EMIM][OTf]
[EMIM][OTf]
[EMIM][BF4]
Et3N3HF
Et3N3HF
Et3N3HF
Et3N3HF
Et3N3HF
Et3N3HF
Et3N3HF
4
4
4
3
4
4
3.5
Yield (%)
A
44
86
6
9
44
83
65
22
72
Trace
Scheme 10.
Fuchigami and his co-workers have reported selective uorination of 4-thiazolidinones and subsequent conversion of our
thiazolidinones to our-lactams which are of pharmaceutical
importance [71,72]. Electro uorinations of b-lactams [73]
Table 8
Historical development in the selective electrochemical uorination of organic compounds [10].
Year
Subtract
Solvent, supporting,
electrolyte
Product
Yield %
Reference
1953
1955
1955
PhC5
5CH2
CH3CH2COOH
CCl25CCl2
Ph2CF-CH2F
CH2FCH2COOH
CFCl2-CFCl2
70
Trace
[60]
[61]
[62]
1960
1970
Ph2C5
5CH2
KHF2-ACOH
AHF
HF-MeCN
HF-ETOH
HF-AcOH
AgF/MeCN
Et3NHF-MeCN
Ph2CF-CH2F
4.5
[63]
[64]
1970
Et4NHF-MeCN
40
[65]
1971
Et4NHF-MeCN
12
[66]
1979
30%Py70%HF
[67]
70
50
35
[68]
[69]
1982
1984
Et2NP(OET)2
pMeOC6H4CH2CN
(EtNH2)SiF6
(Et3N3HF-MeCN)
1990
PhSCH2CF3
Et3N3HF-MeCN
(EtO)2POF
p-MeOC6H4CHCN
p-MeOC6H4CHCN
PhSCHCF3
[70]
Z.U.H. Khan et al. / Journal of Industrial and Engineering Chemistry 31 (2015) 2638
33
Scheme 11.
Scheme 12.
Table 9
Physical and electrochemical properties of ionic liquids (25 8C) [71].
Potential window (V vs Li+Li)c
Ionic liquid
Density (g/cm3)
Viscosity (mPa s)
Conductivity (mS/cm)
Ered (v)
Eoxi (v)
[emim][AlCl4]
[emim][H2.3F3.3]
[emim][BF4]
[emim][CF3CO2]
[emim][CH3SO2]
[emim][CF3SO2]
[emim][CF3SO2)2N]
[emim][C2F5SO2)2N]
[emim][(CF3SO2)3C]
8
9.0
11
14
39
10
15
1
39
1.29
1.14
1.24
1.29b
1.25
1.38
1.52
18
5
43
35a
160
43
28
61
181
22.6
10.00
13.0
9.6a
2.7
9.3
8.4
3.4
1.7
1.0
1.5
1.0
1.0d
1.3d
1.0
1.0
0.9
1.0
5.5
5.3
5.5
4.6d
4.9d
5.3
5.7
5.8
6.0
a
b
c
d
20 8C.
22 8C.
GC (glassy Carbon), 1 mA cm2, 20 mV s2.
pt, 50 mV, emim = 1-ethyl-3-ethyldazolium.
Z.U.H. Khan et al. / Journal of Industrial and Engineering Chemistry 31 (2015) 2638
34
Scheme 13.
Table 10
Conductivity of poly (hydrogen uoride) salts [75].
Table 14
Media effect on anodic uorination of 3-phenylthiophthalide (1).
Conductivity (mS/cm)
Me4NF4HF
Et4.NF4HF
Pr00 4NF4HF
Pr00 4NF4HF
Me3N3HF
197.6
99.2
33.2
9.7
32.8
Run
Reaction media
1
2
3
4
5
Et3N3HF
Et3N4HF
Et3N5HF
Et4N4HF
Et4N5HF
4.2
4.2
3.2
3.3
4
Determined by
Yield (%)a
2
4
77
96
99
93
21
19
FNMR.
Table 11
Fluorination of phthalate (1a) under various conditions [44].
Run
Reaction
media
Supporting electrolyte
Charge
passed (F/mol)
Yield (%)
1
2
3
4
5
6
7
8
MeCN
CH2Cl2
DME
[emim][OTf]
[emim][OTf]
[emim][OTf]
Et3N5HF
Et3N5HF
Et4NF4HF
Et3N3HF
Et3N5HF
Et3N3HF
Et4NF4HF
Et3N5HF
6
8
8
4
8
6
4.7
4
16
23
0
17
16
78
70
90
Scheme 14.
Table 12
Effect of supporting electrolyte on anodic mono-ourination of 1-phenyl-3(phenylthio)oxiindole [85].
Run
Supporting electrolyte
Yield (%)
1
2
3
4
5
Et3N2HF
Et3N3HF
Et4NF2HF
Et4NF3HF
Me4NF4HF
6
6
4
3.7
3.5
3
30
41
58
64
Table 13
Anodic uorination of 2-cyano1-methylpyrrole (1) using various uoride supporting salts in MeCN [85].
Run
Supporting electrolyte (1 M)
1
2
3
4
Et3N2HF
Et3N3HF
Et35HF
Et4NF4HF
Yield(%)a
2
20
5
0
0
Trace
2
12
21
32
65
5
6
Trace
3
54
28
Scheme 15.
Z.U.H. Khan et al. / Journal of Industrial and Engineering Chemistry 31 (2015) 2638
35
Scheme 16.
Z.U.H. Khan et al. / Journal of Industrial and Engineering Chemistry 31 (2015) 2638
36
Scheme 18.
Table 15
Fluorination of O-methyl S-benzyl thio carbonate (1a).
Run
Solvent
Electricity (F/mol)
Yielda (%)
3a
2a
1
2
3
4
5
6
7
8
9
10
11
12
a
b
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
DME
DME
Determined by
Isolated yield.
19
Et4NF-4HF
Et4NF-5HF
Et4NF-4HF
Et4NF-4HF
Et4NF-4HF
Et4NF-4HF
Et4NF-4HF
Et4NF-4HF
Et4NF-4HF
Et3NF-5HF
Et4NF-4HF
Et3NF-5HF
10
10
10
10
5
5
15
15
10
10
10
10
4
4
5
7
4
6
5
6
4
4
4
4
50 (38)
17
28
9
37
25
40
28
17
20
38
22
Trace
0
3
6
0
1
4
4
0
0
0
0
F NMR.
Anodic mono uorination was studied in detail while using Nacetyl-2-oxazolidinone (2a) as reference compounds. The uorination process was carried out in undivided cell, using MCN as
solvent and variation of current. During the process Et4NF-5HF was
used as supporting as well sources of Fluoride ion sources. a-mono
uorinated 4a product was obtained through electrochemical
methods. Figs. 5 and 6 showed the relation of current passed and
percentage of products yield [92].
Fig. 5. Relationship between the yield of 4a and electricity, Current density: 15.
Z.U.H. Khan et al. / Journal of Industrial and Engineering Chemistry 31 (2015) 2638
37
Fig. 6. Relationship between the yield of 4a and current density. Electricity: 15 F/mol.
Scheme 19.
Scheme 21.
38
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Acknowledgment
The authors are thankful to China Scholarship Council (No.
2012GXZ174) and the Fundamental Research Funds for the Central
Universities (YS1406) for support of this research work.
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