Electrochemical partial fluorination of organic compounds: 81. Regioselective anodic fluorination of O-methyl S-aralkyl thiocarbonates

The effect of substituents and operating conditions on the electrochemical fluorination of alkyl phenylacetates in Et3N·4HF medium

“…Quite recently Yoneda co-workers have reported 17% yield during the selective electrochemical fluorination of ethyl phenylacetate in dichloromethane using different supporting electrolytes [11]. A brief report by Cao and Fuchigami is also available [12].…”

Ionic liquids based fluorination of organic compounds using electrochemical method

“…Figure 5 and A c c e p t e d M a n u s c r i p t Figure 6 showed the relation of current passed and percentage of products yield [100]. Quite recently successfully cyclic α-mono Fluoro phosphate esters were prepared by using anodic fluorination and ring-closing Olefin metathesis as shown in scheme 19 [101,102].…”

“…However, if stable Et 4 NF·4HF is used, both the current efficiency and the percentage yield increase in anhydrous MCN electrolytic solution, as shown in scheme 20 [101][102][103][104][105][106].…”

The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives

“…On the other hand, Simonet and co-workers reported the anodic fluorination of alkyl phenyl sulfides having an EWG on the phenyl group in Et 3 N·3HF/MeCN to provide α-monofluorinated products in moderate yields [ 20 ]. We also achieved the anodic fluorination of benzyl and ethyl thiocyanates as well as O -methyl S -aralkyl thiocarbonates by using the anodically stable Et 3 N·5HF and Et 4 NF·4HF [ 21 – 22 ]. In both cases, an EWG attached to the phenyl group and the electron-withdrawing SCN group both contribute to the generation of the cation resulting in a regioselective α-fluorination.…”