Photocatalytic cross-couplings via the cleavage of N–O bonds

Abstract

N-(Acyloxy)phthalimide and oxime derivatives containing N–O bonds are important chemicals and synthetic intermediates, and visible light photoredox reductions of the N–O bonds provide carbon- or nitrogen-centered radicals for N-(acyloxy)phthalimide derivatives and iminyl radicals for oxime derivatives. This feature article summarises the recent progress in the visible light photoredox organic reactions, including decarboxylative addition reactions, alkylation, allylation, alkenylation, alkynylation, arylation, heteroarylation and cascade annulation of N-(acyloxy)phthalimide derivatives through the formation of carbon–carbon bonds, decarboxylative borylation, amination, oxygenation, sulfuration, selenylation, fluorination and iodination of N-(acyloxy)phthalimide derivatives through the formation of carbon–heteroatom bonds, and additions to arenes and alkenes, hydrogen atom transfer and the cleavage of α-carbon–carbon bonds via the iminyl radical intermediates for oxime derivatives.