Cobalt-Catalyzed Oxidative C(sp3)-H Phosphonylation for α-Aminophosphonates via C(sp3)-H/P(O)-H Coupling

Binzhou Lin; Shanshan Shi; Rongcan Lin; Yiqun Cui; Meijuan Fang; Guo Tang; Yufen Zhao

doi:10.1021/acs.joc.8b00674

Cobalt-Catalyzed Oxidative C(sp³)-H Phosphonylation for α-Aminophosphonates via C(sp³)-H/P(O)-H Coupling

J Org Chem. 2018 Jun 15;83(12):6754-6761. doi: 10.1021/acs.joc.8b00674. Epub 2018 May 29.

Authors

Binzhou Lin¹, Shanshan Shi¹, Rongcan Lin¹, Yiqun Cui¹, Meijuan Fang², Guo Tang¹, Yufen Zhao¹

Affiliations

¹ Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province , Xiamen University , Xiamen , Fujian 361005 , China.
² Fujian Provincial Key Laboratory of Innovative Drug Target Research, School of Pharmaceutical Sciences , Xiamen University , Xiamen 361000 , China.

PMID: 29786437
DOI: 10.1021/acs.joc.8b00674

Abstract

The first oxidative C(sp³)-H phosphonylation of tertiary aliphatic amines has been developed. The use of cobalt acetate as a catalyst, N-hydroxyphthalimide as a cocatalyst, and air as an oxidant enabled the conversion of tertiary aromatic and aliphatic amines into α-aminophosphonates in moderate to excellent yields under mild conditions via a cross dehydrogenative coupling reaction.

Publication types

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