Regiodivergent Electrophotocatalytic Aminooxygenation of Aryl Olefins

A method for the regiodivergent aminooxygenation of aryl olefins under electrophotocatalytic conditions is described. The procedure employs a trisaminocyclopropenium (TAC) ion catalyst with visible light irradiation under a controlled electrochemical potential to convert aryl olefins to the corresponding oxazolines with high chemo- and diastereoselectivity. With the judicious choice between two inexpensive and abundant reagents, namely water and urethane, either 2-amino-1-ol or 1-amino-2-ol derivatives could be prepared from the same substrate. This method is amenable to multigram synthesis of the oxazoline products with low catalyst loadings.

Automated summary

A method for the regiodivergent aminooxygenation of aryl olefins under electrophotocatalytic conditions is described, which utilizes a trisaminocyclopropenium ion catalyst and visible light irradiation to convert aryl olefins to oxazoline products with high selectivity. By choosing between water and urethane as reagents, different derivatives of 2-amino-1-ol or 1-amino-2-ol can be synthesized from the same substrate.