4.7 Article

Organophosphorus-Catalyzed Dual-Substrate Deoxygenation Strategy for C-S Bond Formation from Sulfonyl Chlorides and Alcohols/Acids

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 13, Pages 8628-8635

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c00532

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A green method for constructing C-S bonds using sulfonyl chlorides and alcohols/acids via a P-III/P-V=O catalytic system is reported. The organophosphorus-catalyzed umpolung reaction promotes the proposal of a dual-substrate deoxygenation strategy. The method demonstrates the deoxygenation of sulfonyl chlorides and alcohols/acids driven by P-III/P-V=O redox cycling and shows high functional group tolerance, making it applicable for late-stage diversification of drug analogues.
A green method to construct C-S bonds using sulfonyl chlorides and alcohols/acids via a P-III/P-V=O catalytic system is reported. The organophosphorus-catalyzed umpolung reaction promotes us to propose the dual-substrate deoxygenation strategy. Herein, we adopt the dual-substrate deoxygenation strategy, which achieves the deoxygenation of sulfonyl chlorides and alcohols/acids to synthesize thioethers/thioesters driven by P-III/P-V=O redox cycling. The catalytic method represents an operationally simple approach using stable phosphine oxide as a precatalyst and shows broad functional group tolerance. The potential application of this protocol is demonstrated by the late-stage diversification of drug analogues.

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