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Volume # 1(26), January - February 2003 — "The electrolytic method of fluorination in the medium containing the complexes of anhydrous hydrogen fluoride and trialkylamines."
Back to volume # 1(26) , January - February 2003

Fluorine Notes, 2003, 26, 1-2

The electrolytic method of fluorination in the medium containing the complexes of anhydrous hydrogen fluoride and trialkylamines.

G.G.Furin

Novosibirsk Institute of organic chemistry named after N.N.Vorozhtsov 

Siberian branch of the Academy of Science of Russian Federataion


Fax: +7-3822-344752

e-mail: furin@nioch.nsc.ru

ABSTRACT

        The review generalizes and systematizes the latest date on fluorination of the various classes of organic compounds by the electrolytic anodic oxidation method in the medium of electrolyte – the complexes of anhydrous hydrogen fluoride and trialkylamines. An analysis was performed of the basic achievements of the method of one atom fluorine introduction. The facts having an influence on the process and influence of electron-seeking substitutes arranged by CH-fragment and by heteroatoms of VIA group are shown. The examples are given of the useful applications of this method for the synthesis of aromatic and heterocyclic compounds as well as compounds having XCHF fragments, where X=S, Se, Te, as the potential intermediate products for synthesis of the preparations possessing a biological activity. The new efficient production methods of monofluorine – containing organic compounds and their role in organic synthesis are discussed.

Contents

Introduction
1. Electrolytic fluorination of organic compounds in the presence of the electrolyte containing the complexes of   anhydrous hydrogen fluoride and trialkylamines.
    1.1  Anodic monofluorination of aromatic compounds
    1.2  Electrolytic fluorination of heterocyclic compounds.
    1.3. Anodic fluorination of the organic compound with CH-fragment containing electron-seeking substitutes.
 2. Behavior of organic derivatives of the VI group elements, having CH-fragment in alpha position to heteroatom in the electrolytic solutions containing hydrogen fluoride.

Conclusions

References



2. Behaviour of organic derivatives of elements of VI group, having CH-fragment in -position to heteroatom , in electrolyte solutions, containing anhydrous hydrogen fluoride

Anodic fluorination of sulfides, containing RCO and Ph groups, in Et3N* 3HF / MeCN system at 1,1 V results in forming of -fluoroderivatives [108]. Thus, monofluoroderivative 32 and difluoroderivative 33 are produced out of compound 31.

Sulfide E, eV F/mol-1 Yield, %
R1 R2 R3
PhCO H Ph 1,10 1,6 87
Ph COOEt Ph 1,10 6,9 84
COOEt H CH2COOEt 1,46 4,0 50
 

Table 11. Organic compounds fluorination (electrolyte Et3N*3HF, MeCN) [44].

Other sulfides, containing electron-seeking substituents are also subject to anodic monofluorination [64]. The information is given in table 12.

Table 12. Anodic oxidization of sulfides in the presence of Et3N .3HF/MeCN [64].

Substrate Potential of anode, V
vs SSCE		 F/моль Product,
(yield, %)
C6H5SCH2COOEt 1,6 2,5 C6H5SCHFCOOEt (76)
4-MeC6H4SCH2COOEt 1,6 2,1 4-MeC6H4SCHFCOOEt (78)
PhCH2SCH2COOEt 2,1 5,0 PhCH2SCHFCOOEt (44)
n-C7H15SCH2COOEt 2,1-2,3 16,1 n-C7H15SCHFCOOEt (70)
PhSCH2CN 1,7 5,0 PhSCHFCN (75)
PhSCH(COOEt)2 2,0 15,4 PhSCF(COOEt)2 (77)
PhSCH2COMe 1,6-1,8 7,6 PhSCHFCOMe (80)
PhSCH(COMe)2 1,7 3,0 PhSCHFCOMe(55)

Fuchigami with colleagues has done his bit in understanding of anodic fluorination process passing ways [100,109].

The presence of phenyl or the electron-seeking substituent in -position to sulfur atom is necessary [48,64,108,110].

Table 13. Anodic fluorination of arylalkylsulfides [110].

X R Epox Potential of anode, V Q, F/mol Yield, %
MeO CF3 1,49 1,7 6,0 56
H CHF2 1,69 2,3 4,0 53
H CH2F 1,58 2,1 2,7 60
H CF2Cl 1,80 2,0 5,0 43
H H 1,51 1,6 4,0 27
H CH3 1,48 1,8 4,0 18

The system in which anodic fluorination is conducted is really important. Thus, by example of anodic monofluorination of aryl-2,2,2-trifluoroethylsulfide the increasing of fluorination product yield at transfer from Py* n(HF) system to Et3N* 3HF [110] system is registered.

X electrolyte Potential of anode, V
vs SSCE		 F/mol Yield, %
H Py*nHF +2.0 4,1 0
H Bu4NF*3H2O +2.0 1,9 0
H Et3N*3HF +1.9 3,2 62
Cl Et3N*3HF +2.0 7,2 65
Me Et3N*3HF +2.1 8,2 51

It is interesting that anodic fluorination of benzylfluoroalkylsulfides in Et3N* 3HF/MeCN system results in forming of two regio-isomers [110].

Rf Potential of anode, V
vs SSCE		 F/mol Products yield, %
PhCH2SCHF>Rf PhCHFSCH2Rf
CF3 +2.5-2.8 4.0 22 32
CF3 +2.3 11.5 26 45
CF3 +2.3 17.0 51 30
CH2F +2.5-2.7 3.0 13 34

Selective anodic fluorination of ethylphenylsulfanylacetate can be conduct in the flaw-type electrolyzer  at constant potential as well as in galvanostatic mode using anodes from OPTA, Pt or carbon in electrolyte Et3N* 3HF and current density 15 mA/cm2 (yield of monofluorination product is 61, 51 and 49 % accordingly) [98]. Anodic fluorination of sulfides, having electron-seeking substituents in -position to sulfur atom (such groups as cyan, ethers, acyl and phosphates), enables to introduce selectively fluorine atom into the same position [97]. 

The highest yield of fluorination products is achieved in case of fluorination of PhSCH2CONHPr (88 %) [97], 4-MeC6H4SCH2COOEt (78 %) [111] and PhSCH2COPh (87 %) [108]. Mentioned way can be successfully used for fluorination of -phenylthiosubstituted cyclic carbonyl compounds as well as for obtaining of ,-difluoroderivatives  of ethyl--phenylthioacetate 

The monofluorination mechanism of sulfur-containing compounds was not adequately explored. [6,8,9,64]. Many authors consider, that the process includes one-electrone oxidization of substrates with forming of cation-radical. Subsequent steps of the process can pass in two: ether by elimination of proton with generation of active radical, which oxidizes to cation under the action of current with generation of  sulfinic cation, which later reacts with fluoride-ion with forming of reaction product or direct attack of carb-cation center by fluoride-ion occures

.

Selenium-containing compounds also react the same (table 14) [15,64,100,109,112-116].

The best results for compounds XC6H4SeCH2R ( X = H, Cl, MeO) are achieved if electron-seeking groups act as R (R = CN, COOEt, CONH2) [116].

At the same time anodic fluorination of tellurium derivatives in Et3N*3HF (Pt electrodes, current density 12.5 mA/cm2 , anodic potential 1,5 V) in conditions of galvanostatic electrolysis do not result the substitution of hydrogen, which  in -position to tellurium, but the fluorination of tellurium atom occures, accompanied by its oxidization up to quadrivalent state and forming of difluoroderivative [117]. At that the nature of solvent slightly influences the yield of final fluorination product.

Interesting example of electrolytic fluorination is described in works [69,118], when at carbon atom there are two phenyl groups and two SPh groups. In this case the substitution of SPh groups for fluorine atoms occurs .

Table 14. Anodic fluorination of phenylselenides [64].

Substrate Potential of anode,V F/mol Yield, %
PhSeCH2CN 1,6-1,8 6.6 71
PhSeCH2COOEt 1.5 5.8 70
ClC6H4SeCH2COOEt 1.8-1.9 6.5 81
PhSeCH2COCH3 1.6-1.7 3.5 37
PhSeCH2CONH2 1.5-1.6 3.5 60
PhSeCH2Ph 1.3-1.5 20 traces
PhSeCH(CH3)COOEt 1.6 3.1 3
PhSeCH(CH3)CN 1.7-2.0 3.3 16
PhSeCH(COOEt)2 1.8 2.7 55
PhSeCHClCOOEt 2.3 3.0 65

Anodic desulfurization of  ketone dithioacetals in the presence of Et3N*3HF system produces hem-difluorothioethers  and monofluorothioethers [69]. Thereby it is necessary to use the behavior of sulfur-containing compounds carefully. At the same time this is an interesting substitution example of sulfur-containing group for fluorine atom.

Sulfur-containing substitutes influence on anodic fluorination process is typical not only for aromatic compounds, but also for heterocyclic ones. Thus, electrolytic fluorination of 2-benzothiazolyl- and 5-chloro-2-benzothiazolyl-   sulfides using Et4NF*3HF system in dimethoxyethane (DME) produces appropriate -monofluorinated sulfides [119].

X H H H Cl Cl Cl
Z CN CO2Me COMe CN CO2Me COMe
Yield, % 48 62 46 51 82 58

Laurent [108] and  Fuchigami with their colleagues [64,86,109,120] discovered the formation of -monofluoroderivative sulfides during anodic selective fluorination of nitrogen-containing heterocyclic sulfides, which have electron-seeking substituent in methene group. Thus, the conduction of impulse electrolysis of pyridine and pyrimidine derivatives in Et3N*3HF/MeCN medium with Pt electrodes at 25 oC results in formation of monofluoroderivatives [114,120].

X R Potential of anode, V
vs SSCE		 F/mol  Yield, % 
CH CN 1.6 5 76
CH COOEt 1.6 5 76
CH H 1,6 5 traces
CH CH2CN 1.6 6 traces
CH PO(OEt)2 1.6 6 traces
CH SMe 1.6 5 traces
N COOEt 2.2 11 55

Pyridine derivatives, having in -position SCH2R group, are also subject to anodic fluorination with formation of monofluoroderivatives [114].

The presence in -position CN group (2-pyridylsulfide 34) allows to obtain (in the presence of base) bicyclic heterocycle 2-fluorothieno[2,3-b] pyridine 38. The reaction must pass as follows: at first -fluoromethylpyridylsulfide  35 forms due to anodic fluorination of 2-pyridylsulfide 34. Thienopyridinimine 36 is formed in the base medium. This compound reacts with ethyl alcohol and  produces intermediate compound 37, which aromatization with elimination of diethylcarbonate results in formation of compound 38.

We'll note, that fluorination of these heterocyclic compounds by such fluorine reagents as triphthalate N-fluoropyridinium  and N-fluoro-3,5-dichloropyridinium  proved to be ineffective [121].

Electrochemical anodic fluorination of 4(7-trifluoromethyl)quinolylsulfides 39  was realized in Et4NF*nHF (n=3,4) and Et3N*3HF systems  in  dimethoxyethane.  Corresponding -monofluoroderivatives of these sulfides 40 are obtained with good yield (table. 15) [122]. For the case X = COMe  the formation of compound 41 take place too (yield 7 %).

For 2-quinolylsulfides 42  the formation of three compounds 43-45 take place (table 16).

Table 15. Anodic fluorination of 4(7-trifluoromethyl)quinolylsulfides (dimethoxyethane) [122].

X Eoxp (V vs SSCE)
Pt-electrode
0,1M Bu4NBF4		 Electrolyte F/mol Yield of 40,%
COMe 1,92 Et4NF*3HF
Et4NF*4HF		 4
2,5		 96
62
COOEt 2,04 Et4NF*3HF
Et3N*3HF		 4,5
6		 83
67
CN 2,14 Et4NF*4HF
Et4NF*3HF
Et3N*3HF		 4
4
6		 86
87
77

Table 16. Anodic fluorination of 2-quinolylsulfides [122]

X

 Eoxp (V vs SSCE)
Pt-electrode
0,1M Bu4NBF4		 Electrolyte F/mol Product's yield, %
43 44 45
COMe 1,7 Et4NF*4HF
Et4NF*3HF
Et3N*3HF
Et3N*3HF
Et3N*3HF		 4
6
7
6
4		 54
50
55
64
28		 8
8
8
-
-		 5
5
5
-
-
COOEt

1,76

Et4NF*4HF
Et4NF*3HF
Et3N*3HF

4
4
6

 62
64
59		   5
5
7
CN

1,91

Et4NF*4HF
Et4NF*3HF
Et3N*3HF

 8
8
8		 61
52
62		   12
12
12

The solvent's influence on this reaction has been studied by Fuchigami [123]. It turned out, that dimethoxyethane is the best solvent, acetonitrile is less effective though it’s mixture with dimethoxyethane gives quite good results.

If in heterocyclic ring there is SMe groups the poor yield substitution of hydrogen from methyl group by fluorine take place.

It should be noted, that such acknowledged fluorinating agents as N-fluoropyridinic salts  [124] showed absolute inertness at present objects. This allows to consider electrochemical fluorination as alternative method for known fluorination processes and its further development and application to other organic substrates can be expected.

Thus, the new approach to synthesis  of hard-to-reach derivatives of sulfur and selenium with S-CHF и SCF2, Se-CHF fragments is developed, some of which are high biologically active [121]. In spite of seemed vagueness regarding commercial application the fluorination by electrolyte method continues to attract active interest of researchers. The opportunity of moving the fluorination centre from aromatic cycle onto functional groups, containing, for example active methene group, creates real perspectives for development of convenient synthesis method of hard-to-reach monofluoroderivatives. Polyfluorinated hydrocarbon synthesis using this method seems to be workable, that by all means is important.

-Fluorocontaining derivatives of aromatic compounds with C=O and S-R-groups are increasingly biologically active. Their synthesis is carried out by fluorination using xenon difluoride [125-127], DAST [124,128], triphthalate N-fluoropyridinium , particularly N-fluoro-2,4,6- trimethylpyridinium  triphthalate and N-fluoro-3,5-dichloropyridinium triphthalate   [29]. However these methods give lower yields and poor results comparing to anodic fluorination method.

Dimethoxyethane and dimethyl ether of diglycol at anodic fluorination in electrolytes Et3N*5HF and Et4NF*4HF give either mixtures of isomeric fluoroethers  or monofluoroderivative with fluorine atom located in the beginning of carbon chain [61].

As a whole, electrochemical fluorination method as way to low-fluorinated derivatives continues to attract the attention of researchers, in spite of today’s vagueness regarding commercial application.

Conclusion

The presented material allows to make a conclusion that electrochemical monofluorination in electrolytes - the complexes of anhydrous hydrogen fluoride and trialkylamines - is an important method of obtaining of monofluorinated organic compounds, which opportunities steadily increase as far as present method improves. At this different classes of compounds are entered into reaction, that resulted in noticeable success of aromatic and heterocyclic monofluorinated derivatives synthesis. The materials obtained have found practical application. Because of importance of these organic compounds classes the improvement tasks of their obtaining technology are urgent and stimulated by requirements of techniques. Obviously, the further research in this field will go on both in extension of started before aspects of electrochemical process itself and in transfer to fundamentally new decisions and approaches. Here it is important not only to formulate common rules of organic compounds behavior in electrochemical fluorination process but also try to reveal the specific particularities properties of the process, caused by fluorine atoms. Such substrates, as can be seen from stated above, are noticeable more persistent in anodic oxidization conditions and give noticeable higher outputs, that no doubt simplifiers the stage of target product extraction. Thorough researches for development of our knowledge of electrochemical fluorination mechanism should mean a lot. 


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