Organic Letters
Organic Letters
5 years ago

Radical Difluoromethylation of Thiols with (Difluoromethyl)triphenylphosphonium Bromide

Radical Difluoromethylation of Thiols with (Difluoromethyl)triphenylphosphonium Bromide
Niklas B. Heine, Armido Studer
A method for facile difluoromethylation of various thiols using (difluoromethyl)triphenylphosphonium bromide under mild reaction conditions is presented. The transformation proceeds in the absence of any transition metal using a bench-stable and readily accessible phosphonium salt. Deuterium labeling experiments and cyclic voltammetry measurements reveal that the difluoromethylation occurs via a SRN1-type mechanism. Substrate scope is broad, and various functional groups are tolerated (OH, NH2, amide, ester).

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02109

DOI: 10.1021/acs.orglett.7b02109

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