Cu(I)-Catalyzed Radical Coupling of Alkenes with Sulfonimidoyl Chlorides: Synthesis of Vinyl Sulfoximines

A Cu(I)-catalyzed radical coupling was reported for the synthesis of vinyl sulfoximines from sulfonimidoyl chlorides and alkenes under mild, light-free conditions. This method proceeds via a sulfonimidoyl radical intermediate, generated through Cu(I) reduction, and demonstrates broad substrate tolerance, delivering products in up to 84% yield. The transformation could also be efficiently conducted in a practical one-pot manner by generating the sulfonimidoyl chloride in situ from the S(IV) sulfonamide. Moreover, the addition of <i>t</i>BuOCl further improved the yields of vinyl sulfoximines for several substrates. Mechanistic studies support a radical pathway involving this key sulfonimidoyl radical species.