Primary Amination of Ar₂P(O)-H with (NH₄)₂CO₃ as an Ammonia Source under Simple and Mild Conditions and Its Extension to the Construction of Various P-N or P-O Bonds

Yushi Tan, Ya-Ping Han, Yuecheng Zhang, Hong-Yu Zhang*, Jiquan Zhao* and Shang-Dong Yang

*School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, P. R. China, Email: zhanghyhebut.edu.cn, zhaojqhebut.edu.cn

Y. Tan, Y.-P. Han, Y. Zhang, H.-Y. Zhang, J. Zhao, S.-D. Yang, J. Org. Chem., 2022, 87, 3254-3264.

DOI: 10.1021/acs.joc.1c02933

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Abstract

Ethyl bromoacetate mediates a facile and efficient synthesis of primary phosphinamides from Ar₂P(O)-H reagents with stable and readily available ammonium carbonate as an ammonia source under mild and simple conditions, without any metal catalyst or oxidant. Moreover, this method is also appropriate for the reaction of Ar₂P(O)-H with a variety of amines, alcohols, and phenols.

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proposed mechanism

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Key Words

phosphinamides, phosphinates

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ID: J42-Y2022