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Radical Difluoromethylation of Thiols with (Difluoromethyl)triphenylphosphonium Bromide
Niklas B Heine1, Armido Studer1
1Organisch Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstraße 40, 48149 Münster, Germany.
Abstract:
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).
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