TBHP/NH4I-Mediated Direct N-H Phosphorylation of Imines and Imidates

Xiaofeng Wang; Yingcong Ou; Zhenbo Peng; Guodian Yu; Yuanting Huang; Xianwei Li; Yanping Huo; Qian Chen

doi:10.1021/acs.joc.9b02301

TBHP/NH₄I-Mediated Direct N-H Phosphorylation of Imines and Imidates

J Org Chem. 2019 Nov 15;84(22):14949-14956. doi: 10.1021/acs.joc.9b02301. Epub 2019 Oct 25.

Authors

Xiaofeng Wang¹, Yingcong Ou¹, Zhenbo Peng², Guodian Yu¹, Yuanting Huang¹, Xianwei Li¹, Yanping Huo¹, Qian Chen^{1

3}

Affiliations

¹ School of Chemical Engineering and Light Industry , Guangdong University of Technology , Guangzhou 510006 , China.
² Chemical Engineering College , Ningbo Polytechnic , Ningbo 315800 , China.
³ Key Laboratory of Functional Molecular Engineering of Guangdong Province , South China University of Technology , Guangzhou 510640 , China.

PMID: 31622097
DOI: 10.1021/acs.joc.9b02301

Abstract

A direct and practical metal-free N-H phosphorylation has been achieved via the TBHP/NH₄I-mediated cross-dehydrogenative coupling (CDC) reactions between imines/imidates and P(O)H compounds. This transformation provides an efficient synthetic route to the construction of P-N bonds with good functional group compatibility, leading to the formation of N-phosphorylimines and N-phosphorylimidates in up to 95% yield (33 examples) under mild conditions.

Publication types

Research Support, Non-U.S. Gov't