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Updated: Apr 25, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Copper-catalyzed three-component radical relay alkenylation of sulfenamides
Renkang Wei1, Jing Zhong1, Qian Wang1
1State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing 210009, P. R. China. hyao@cpu.edu.cn.
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.
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