Synthesis of gem-difluoroalkenes via photoredox-catalyzed defluoroaryloxymethylation of α-trifluoromethyl alkenes

Abstract

Herein, we present a novel method for the synthesis of gem-difluoroalkenes via visible-light photoredox-catalyzed defluoroaryloxymethylation of α-trifluoromethyl alkenes using α-silyl ethers as aryloxymethyl radical precursors. This reaction shows good functional group tolerance and provides the desired products in good to excellent yields. Based on mechanistic studies, we propose a reaction mechanism involving single-electron oxidation of an α-silyl ether to generate an α-aryloxymethyl radical.