Visible light-induced metal-free chemoselective oxidative cleavage of benzyl C–heteroatom (N, S, Se) bonds utilizing organoboron photocatalysts

Abstract

The oxidation process is widely explored and used to synthesize diverse organic chemicals. Herein, a unified metal-free photooxidative platform for the cleavage of C–heteroatom bonds has been developed. In these reactions, the aminoquinolate diarylboron (AQDAB) complex is utilized as the photocatalyst, instigating the oxidation process induced by visible light. The cleavage of C–heteroatom bonds can be achieved chemoselectively, affording the formal carbonylation product of C–N, C–S, and C–Se bonds. This method provides a channel for connecting amines, thiols, or selenides with the carbonyl compounds directly, broadening the potential applications of oxidation as a synthetic tool.