Metal-free photoredox-catalyzed direct α-oxygenation of N,N-dibenzylanilines to imides under visible light

An efficient synthesis of imides using metal-free photoredox-catalyzed direct alpha-oxygenation of N,N '-disubstituted anilines in the presence of 9-mesityl-10-methylacridinium [Acr(+)-Mes]BF4 as a photoredox catalyst and molecular oxygen as a green oxidant under visible light was developed. This photochemical approach offered operational simplicity, high atom economy with a low E-factor, and functional group tolerance under mild reaction conditions. Control and quenching experiments confirmed the occurrence of a radical pathway and superoxide radical anion alpha-oxygenation reactions, and also provided strong evidence for the reductive quenching of [Acr(+)-Mes]BF4 based on a Stern-Volmer plot, which led to the proposed mechanism of this reaction.

Automated summary

An efficient method for the synthesis of imides using metal-free photoredox-catalyzed direct alpha-oxygenation of N,N'-disubstituted anilines has been developed. This method offers operational simplicity, high atom economy, and functional group tolerance under mild reaction conditions.