Photoinduced amination of iodoalkanes enabled by bifunctional O-benzoyl oxime

Abstract

Herein, we proposed a practical synthetic method for the efficient preparation of primary and secondary alkyl amines from alkyl iodides and easily accessible O-benzoyl oxime. O-Benzoyl oxime acts as a bifunctional reagent undergoing photocatalytic energy transfer-driven homolysis followed by decarboxylation to produce persistent iminyl radicals and aryl radicals, which undergo halogen atom transfer (XAT) with iodoalkanes. Further selective radical–radical C–N cross-coupling with iminyl radicals generates valuable amine building blocks. Hydrolysis of the imine could directly lead to the corresponding primary amine. Mechanistic studies have demonstrated that the reaction involves a free radical chain process.