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

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.

Automated summary

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.