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)2(dtbbpy)]­PF6 with i-Pr2NEt as the reducing agent, N-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 i-Pr2NEt to afford the imidazolinone products.