Visible-Light-Driven Aryl Migration and Cyclization of α-Azido Amides.

This paper reports two new visible-light-promoted radical reactions of α-azido amides. By catalysis of [Ir(ppy)(dtbbpy)]PF with -PrNEt as the reducing agent, -aryl α-azido tertiary amides were first converted to the corresponding aminyl radicals through reduction of the azido group; the aminyl radicals then underwent N-to-N aryl migration to give α-anilinyl-functionalized amides. α-Azido secondary amides, on the other hand, reacted with the solvent ethanol and -PrNEt to afford the imidazolinone products.