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; Shang-Dong Yang

doi:10.1021/acs.joc.1c02933

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

J Org Chem. 2022 Mar 4;87(5):3254-3264. doi: 10.1021/acs.joc.1c02933. Epub 2022 Jan 24.

Authors

Yushi Tan¹, Ya-Ping Han¹, Yuecheng Zhang¹, Hong-Yu Zhang¹, Jiquan Zhao¹, Shang-Dong Yang²

Affiliations

¹ School of Chemical Engineering and Technology, Hebei Provincial Key Lab of Green Chemical Technology & High Efficient Energy Saving, Tianjin Key Laboratory of Chemical Process Safety, Hebei University of Technology, Tianjin 300130, P. R. China.
² State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.

PMID: 35073084
DOI: 10.1021/acs.joc.1c02933

Abstract

A facile and efficient method for the synthesis of primary phosphinamides from Ar₂P(O)-H reagents with stable and readily available ammonium carbonate as an ammonia source is disclosed herein for the first time. This ethyl bromoacetate-mediated primary amination proceeds smoothly 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 to construct P-N or P-O bonds, with features of handy operation, good functional group tolerance, and broad substrate scope.