Photoinduced triiodide-mediated [3 + 2] cycloaddition of N-tosyl aziridines and alkenes

Abstract

A metal-free photoinduced triiodide-mediated [3 + 2] cycloaddition of N-Ts aziridines with alkenes is described herein. This operationally simple protocol utilized bench-stable and inexpensive TBAI as a radical mediator, enabling regioselective access to substituted pyrrolidines with good functional group compatibility. Preliminary mechanistic experiments disclosed that TBAI₃, generated in situ from TBAI, promoted the crucial radical ring-opening of N-Ts aziridines.