Cyanohydrin-Mediated Cyanation of Remote Unactivated C(sp³)–H Bonds

Abstract

A new approach for generation of alkoxy radical from the O-H bond of cyanohydrin promoted by visible-light photoredox catalysis is reported. The alkoxy radical triggers the successive remote HAT and intramolecular cyano migration, leading to the regioselective cyanation of remote C(sp³)-H bonds. The reaction exhibits a broad functional group tolerance that allows many sensitive groups to remain intact under mild conditions. To demonstrate the utility of method, the ketonitrile products are converted to other synthetically valuable compounds.