Copper-catalyzed three-component radical relay alkenylation of sulfenamides
Abstract
Herein, we report a copper-catalyzed three-component radical relay alkenylation of sulfenamides with Togni reagent and alkynes. This strategy provides a general and efficient route for the synthesis of chiral β-trifluoromethyl alkenyl sulfilimines in good yields with good chemo-, regio- and stereoselectivity. The resulting alkenyl sulfilimine products can be readily oxidized to access the corresponding chiral alkenyl sulfoximines. Mechanistic studies and density functional theory (DFT) calculations support a radical pathway and identify a concerted hydrogen-atom transfer (HAT) and radical coupling (RC) process as the key stereodetermining step.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Sulfur-Based Synthesis Techniques
Radical Photochemical Reactions
Publication details
- Journal / source
- Chemical Communications
- Publisher
- Royal Society of Chemistry (RSC)
- Volume
- 62
- Issue
- 37
- Pages
- 9442–9446
- Publication date
- 1 January 2026
- Language
- EN