Cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications

• Sadanobu Iwase,
• Shinsuke Inagi and
• Toshio Fuchigami

Beilstein J. Org. Chem. 2022, 18, 872–880, doi:10.3762/bjoc.18.88

• resulted in much lower product yields. The detailed reaction mechanism was clarified based on the cathodic reduction of 1 in the presence of deuterated acetonitrile, CD3CN. Keywords: bis(phenylthio)difluoromethane; cathodic reduction; deuteration; o-phthalonitrile mediator; (phenylthio)difluoromethylation

• cathodic reduction of 1 at a platinum cathode in Bu4NClO4/MeCN. Notably, when 1.3 F/mol were passed, starting compound 1 was consumed completely. As shown in Scheme 4, difluoromethyl phenyl sulfide (2) was mainly formed as well as bis(phenylthio)difluoromethane (3) as a minor product. From these results