Selective C-F bond carboxylation of gem-difluoroalkenes with CO2 by photoredox/palladium dual catalysis

Chem Sci. 2019 May 28;10(27):6721-6726. doi: 10.1039/c9sc01336a. eCollection 2019 Jul 21.

Abstract

The catalytic C-F bond carboxylation of organofluorines with CO2 gas remains a challenging problem in synthetic chemistry. Here, we describe a selective defluorinative carboxylation of gem-difluoroalkenes through photoredox/palladium dual catalysis. The C-F bond activation is enabled by single electron reduction through photoredox catalysis to generate a fluorovinyl radical, which subsequently participates in an unprecedented palladium-catalyzed carboxylation. This novel C-F functionalization proved applicable to a wide range of substituted gem-difluoroalkenes, providing a rapid access to valuable α-fluoroacrylic acids.