Expedient access to α-(hetero)aryl-α-keto-1,3-diamines via redox-neutral photocatalyzed reactions of N-vinylimides with α-aminoalkyl radicals

Abstract

Herein, we report a novel acyl migration protocol based on a reductive radical-polar crossover process enabled by redox-neutral photocatalysis. Employing tertiary amines or α-silylamines as radical sources, modular access to various functionalized α-(hetero)aryl-α-keto-1,3-diamines could be efficiently realized via reactions of enamides with α-aminoalkyl radicals under mild reaction conditions. Additionally, the radical addition/acyl migration cascade process could be extended to the intramolecular version. The synthetic application of acyl migrated products was also demonstrated. Taking advantage of the easy generation of α-aminoalkyl radicals and α-imido carbanions via a single-electron-transfer process, this new procedure features a broad substrate scope and exogenous reductant-free conditions.