Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjia Xiang, Nanjing 210009, China.
J Org Chem. 2023 Jul 7;88(13):8628-8635. doi: 10.1021/acs.joc.3c00532. Epub 2023 Jun 9.
A green method to construct C-S bonds using sulfonyl chlorides and alcohols/acids via a P/P═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/P═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.
本文报道了一种使用亚磺酰氯和醇/酸通过 P/P═O 催化体系构建 C-S 键的绿色方法。有机磷催化的反转反应促使我们提出了“双底物脱氧”策略。在此，我们采用“双底物脱氧”策略，通过 P/P═O 氧化还原循环驱动，实现了亚磺酰氯和醇/酸的脱氧反应，合成了硫醚/硫酯。该催化方法采用稳定的氧化膦作为前催化剂，操作简单，具有广泛的官能团容忍性。该方法的潜在应用通过药物类似物的后期多样化得到了证明。
