Photocatalytic Defluoroalkylation of Trifluoroacetates with Alkenes using 4-(Acetamido)thiophenol

Abstract

Under mild irradiation conditions using violet light-emitting diodes, a catalytic amount of a thiolate of N-(4-mercaptophenyl)pivalamide promotes monoselective defluoroalkylation of trifluoroacetates with a variety of aliphatic alkenes in the presence of a formate salt. The reactions allow facile and low-cost synthesis of valuable α,α-difluoro substituted aliphatic carboxylate esters under mild conditions, and demonstrate the dual-functional role of arenethiolates in photocatalysis as both a strong photoreductant in a redox cycle and a hydrogen-atom-transfer catalyst.

Key words

defluoroalkylation - trifluoroacetate - arenethiolate - dual function catalysts - photoredox catalysis - HAT catalysis

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