Iminyl-Radical-Promoted C–C Bond Cleavage/Heck-Like Coupling via Dual Cobaloxime and Photoredox Catalysis

Abstract

We report herein an unprecedented protocol for radical-olefin coupling of α-imino-oxy acids and alkenes for the synthesis of alkene-containing nitriles via synergistic photoredox and cobaloxime catalysis. With visible-light irradiation, the transformation provides a variety of corresponding alkene-containing nitriles under mild reaction conditions. The C-C bond cleavage/Heck-like coupling reaction could generate <i>E</i>-selective coupling products with excellent chemo- and stereo-selectivity. This iminyl-radical-mediated reaction is external-oxidant-free, exhibits wide functional-group compatibility, and occurs with the extrusion of acetone, H₂, and CO₂.