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Electrochemical C–H phosphorothiolation of indolizines with thiocyanate and phosphite in one pot
Tetrahedron ( IF 2.1 ) Pub Date : 2024-02-22 , DOI: 10.1016/j.tet.2024.133911
Chenglong Feng , Haochen Wang , Yuanbin She , Meichao Li , Zhenlu Shen

A facile and practical protocol for C–H phosphorothiolation of indolizines using thiocyanate as the sulfur source and phosphite as the phosphorylated reagent has been developed. A broad range of substrates were well tolerated and the desired products were obtained in moderate to excellent yields. Moreover, the reaction involved electrochemical thiocyanation of indolizines and a chemical process to construct the S–P bond in the presence of DBU. A plausible EC mechanism for this reaction has been revealed by cyclic voltammetry and control experiments. This method provided a green pathway to synthesize -(hetero)aryl phosphorothioates by electrochemical oxidation at room temperature without external oxidants and transition metal catalysts.

中文翻译:

硫氰酸盐和亚磷酸盐一锅法对中氮茚进行电化学 C-H 硫代磷酸化

已经开发出一种简便实用的中氮茚的 C-H 硫代磷酸化方案,使用硫氰酸盐作为硫源,亚磷酸盐作为磷酸化试剂。多种底物具有良好的耐受性,并且以中等至优异的产率获得了所需的产物。此外,该反应涉及中氮茚的电化学硫氰化以及在 DBU 存在下构建 S-P 键的化学过程。循环伏安法和对照实验揭示了该反应的合理 EC 机制。该方法为室温电化学氧化合成-(杂)芳基硫代磷酸酯提供了一条绿色途径,无需外部氧化剂和过渡金属催化剂。
更新日期:2024-02-22
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