Visible light-induced oxygen atom transfer into C-CL bond of acyl chlorides for homolytic cleavage

Oxygen O(³P) atom has been rarely explored in condensed-phase chemistry, with known examples limited to σ insertion into C - H bonds, alkene epoxidation, and sulphide oxidation. Herein, we report the efficient generation of oxygen O(³P) atom via visible-light-induced deoxygenation of aryl 1H-benzotriazole 3-oxides under mild conditions. We demonstrate that oxygen atom undergoes transfer into the C-Cl bond of acyl chlorides to afford acyl hypochlorites. Two distinct homolytic cleavage pathways, O-Cl bond homolysis and C - O bond homolysis, are identified for hypochlorites derived from either aryl acyl chlorides or alkyl acyl chlorides. On the basis of these findings, the oxygen atom transfer is employed in cascade radical coupling of acyl chlorides with alkenes and silyl enol ethers.