Photoredox-catalyzed multicomponent 1,2-difunctionalization of activated alkenes with silyl enol ethers and oxime esters

Abstract

The photoredox-catalyzed multicomponent 1,2-cyanoalkylacylmethylation of electron-deficient alkenes using silyl enol ethers and cycloketone oxime esters has been described. This protocol provides access to alkyl cyanide group-anchored 1,4-dicarbonyl compounds with generally excellent yields. Furthermore, the 1,2-difunctionalization of acrylates can be achieved by adjusting the types of inorganic bases and replacing cycloketone oxime esters with indanone oxime esters in this catalytic system. Mechanistic studies demonstrated that the transformation proceeds via a radical pathway involving deconstructive carbon–carbon cleavage of oxime esters, radical addition, single-electron oxidation, and a desilylation cascade.