Radical Photochemical Difluorosulfoximination of Alkenes and Propellanes

Abstract

Herein, we report a metal-free divergent visible-light driven method for the synthesis of fluorinated sulfoximines. Both olefins and propellanes efficiently undergo difluorosulfoximination with yields up to 77% (65 examples). The process is general and robust and tolerates diverse functional groups, including esters, ethers, ketones, silyl groups, silyl ethers or boronic esters. The functionalization of diverse bioactive ingredients (8 examples), as well as various products manipulations demonstrate the synthetic usefulness of the developed synthetic platform. Finally, we rationalized the divergent reaction mechanism performing Stern-Volmer quenching and EPR experiments, that revealed the key activity of a difluoroalkyl sulfoximine radical.