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

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 TBAI(3), generated in situ from TBAI, promoted the crucial radical ring-opening of N-Ts aziridines.

Automated summary

This study presents a metal-free photoinduced triiodide-mediated [3 + 2] cycloaddition of N-Ts aziridines with alkenes, utilizing a simple protocol and TBAI as a radical mediator to achieve regioselective access to substituted pyrrolidines with good functional group compatibility. Preliminary mechanistic experiments suggested that TBAI(3) generated in situ from TBAI played a crucial role in promoting the radical ring-opening of N-Ts aziridines.