Electrophotocatalytic Acetoxyhydroxylation of Aryl Olefins

A method for the acetoxyhydroxylation of olefins with syn stereoselectivity under electrophotocatalytic conditions is described. The procedure uses a trisaminocyclopropenium (TAC) ion catalyst with visible light irradiation under a controlled electrochemical potential to convert aryl olefins to the corresponding glycol monoesters with high chemo- and diastereoselectivity. This reaction can be performed in batch or in flow, enabling multigram synthesis of the monoester products.

Automated summary

A method for acetoxyhydroxylation of olefins with syn stereoselectivity under electrophotocatalytic conditions using a TAC ion catalyst has been developed. The reaction, catalyzed by visible light irradiation at controlled electrochemical potential, converts aryl olefins to glycol monoesters with high chemo- and diastereoselectivity. It can be carried out in batch or flow, enabling the synthesis of multigram quantities of the monoester products.