Polychloromethylation-Initiated Radical 1,2-Aryl Migration of α,α-Diarylallyl Alcohols via Visible-Light Photoredox Catalysis

A visible-light induced radical 1,2-aryl migration of & alpha;,& alpha;-diarylallyl alcohols was developed under mild and metal-free conditions. Commercially available CHCl3 and CH2Cl2 were used as tri- and dichloromethyl radical precursors. Structurally diverse & beta;-polochloromethylated ketones were obtained in good to moderate yields via neophyl-type rearrangement. Besides, the polychloromethyl group can be easily transformed into other useful functional groups.

Automated summary

A visible-light induced radical 1,2-aryl migration of α,α-diarylallyl alcohols was developed using commercially available CHCl3 and CH2Cl2 as tri- and dichloromethyl radical precursors under mild and metal-free conditions. This reaction provided structurally diverse β-polochloromethylated ketones in good to moderate yields through neophyl-type rearrangement, and the polychloromethyl group could be easily transformed into other useful functional groups.