Visible-light-promoted sulfonimidation of alkenes and alkynes

Abstract

Vinyl sulfoximines are privileged sulfur-containing scaffolds, valued for their unique reactivity and biological relevance in medicinal and materials chemistry. We report a visible-light-promoted sulfonimidation method for efficient synthesis of vinyl sulfoximines. In this synthesis, sulfonimidoyl chlorides form an electron donor-acceptor complex with iodine, which facilitates sulfoximinyl radical generation under blue LED irradiation. These radicals react with alkenes or alkynes to create the vinyl sulfoximine frameworks. This transition-metal-free method exhibits excellent regio-and stereoselectivity and broad substrate compatibility, including electron-deficient, aromatic, and aliphatic precursors. By overcoming the limitations of traditional methods, particularly sulfonimidating electron-deficient alkenes and alkynes, this method provides a practical, efficient route to vinyl sulfoximines. This work expands the scope of sulfoximinyl radical chemistry and provides a robust tool for applications in drug discovery and molecular design.