Enantioselective Synthesis of Sulfilimines Enabled by Photoinduced Copper-Catalyzed C(sp 3 )-H Sulfimidation
Abstract
Chiral sulfilimines, as a classic type of organosulfur molecule, are indispensable in synthetic chemistry and pharmaceutical applications, underscoring the significance of their catalytic asymmetric synthesis. While asymmetric S -functionalization of sulfenamides has recently emerged as an effective strategy for accessing chiral sulfilimines, feasible approaches that enable the S -chirality to be created via C(sp 3 )-H sulfimidation between sulfenamides and hydrocarbons remain exceedingly rare and synthetically challenging. Herein, we describe a photoinduced copper-catalyzed C(sp 3 )-H sulfimidation, allowing for a straightforward synthesis of highly enantioenriched sulfilimines from simple hydrocarbon feedstocks. Computational studies and mechanistic investigations unveil the outer-sphere S H 2 reaction mechanism of the C–S bond formation step.
Fields of Study & Subjects
Sulfur-Based Synthesis Techniques
Synthesis and Catalytic Reactions
Catalytic C–H Functionalization Methods
Publication details
- Journal / source
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Volume
- 148
- Issue
- 22
- Pages
- 23021–23031
- Publication date
- 25 May 2026
- Language
- EN