Organic photosensitized aziridination of alkenes

Abstract

We report a new TADF-catalyzed aziridination of alkenes under visible light. In this protocol, a free triplet nitrene is in situ generated from the commercially available tosyl azide by energy transfer of the excited photocatalyst 4DPAIPN. Our finding enables the smooth installation of the strained aziridine ring into a remarkably wide scope of alkenes and pharmaceutical-derived olefins and natural products, as well as the synthesis of sitagliptin. This metal-free method provides a new opportunity for the late-stage modification of complex molecules or synthesis of nitrogen-containing pharmaceuticals.