Synthesis of S-Aryl Phosphorothioates by Copper-Catalyzed Phosphorothiolation of Diaryliodonium and Arenediazonium Salts

Liangliang Zhang, Pengbo Zhang, Xueqin Li, Jian Xu*, Guo Tang* and Yufen Zhao

*College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005; College of Chemical Engineering, Huaqiao University, Xiamen 361021, China, Email: xujian2024qq.com, t12g21xmu.edu.cn

L. Zhang, P. Zhang, X. Li, J. Xu, G. Tang, Y. Zhao, J. Org. Chem., 2016, 81, 5566-5573.

DOI: 10.1021/acs.joc.6b00925

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Abstract

Green methods based on copper-catalyzed multicomponent reactions enable the synthesis of S-aryl phosphorothioates from diaryliodonium/arenediazonium salts, elemental sulfur, and R₂P(O)H compounds in very good yields at room temperature. These transformations allow the direct formation of P-S and C-S bonds in one reaction.

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Phosphorothiolation of Aryl Boronic Acids Using P(O)H Compounds and Elemental Sulfur

J. Xu, L. Zhang, X. Li, Y. Gao, G. Tang, Y. Zhao, Org. Lett., 2016, 18, 1100-1103.

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Key Words

phosphorothioates, phosphorothiolation, multicomponent reactions

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ID: J42-Y2016