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

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. We have established a photooxidation system, which can realize formal carbonylation of C-heteroatom (N, S, Se) bonds.

Automated summary

The study developed a unified metal-free photooxidative platform for the cleavage of C-heteroatom bonds, using AQDAB complex as the photocatalyst to induce the oxidation process. This method allows for chemoselective cleavage of C-N, C-S, and C-Se bonds, broadening the potential applications of oxidation in synthetic chemistry. It established a photooxidation system for formal carbonylation of C-heteroatom (N, S, Se) bonds.