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

Herein, we present a novel method for the synthesis of gem-difluoroalkenes via visible-light photoredox-catalyzed defluoroaryloxymethylation of alpha-trifluoromethyl alkenes using alpha-sityl 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 alpha-silyl ether to generate an alpha-aryloxymethyl radical.

Automated summary

In this study, a novel synthesis method for gem-difluoroalkenes was presented through visible-light photoredox-catalyzed defluoroaryloxymethylation of alpha-trifluoromethyl alkenes using alpha-sityl ethers as aryloxymethyl radical precursors. The reaction displayed good functional group tolerance and provided desired products with high yields. Mechanistic studies supported the proposal of a reaction mechanism involving single-electron oxidation of an alpha-silyl ether to generate an alpha-aryloxymethyl radical.