Electrochemical C–H phosphorothiolation of indolizines with thiocyanate and phosphite in one pot

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. Mo...

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Veröffentlicht in:Tetrahedron 2024-04, Vol.155, p.133911, Article 133911
Hauptverfasser: Feng, Chenglong, Wang, Haochen, She, Yuanbin, Li, Meichao, Shen, Zhenlu
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Sprache:eng
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Zusammenfassung: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 S-(hetero)aryl phosphorothioates by electrochemical oxidation at room temperature without external oxidants and transition metal catalysts. A facile and practical protocol without external oxidants and transition metal catalysts for C–H phosphorothiolation of indolizines in a three-component reaction has been developed. This method provided a green pathway to synthesize S-(hetero)aryl phosphorothioates by electrochemical oxidation at room temperature. A broad range of substrates were well tolerated and the desired products were obtained in moderate to excellent yields (up to 87%) with good regioselectivity. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2024.133911