Mn(OAc)3-Promoted Oxidative Csp3-P Bond Formation through Csp2-Csp2 and P-H Bond Cleavage: Access to β-Ketophosphonates

Pan Zhou; Biao Hu; Lingdan Li; Kairui Rao; Jiao Yang; Fuchao Yu

doi:10.1021/acs.joc.7b02391

Mn(OAc)₃-Promoted Oxidative C_sp³-P Bond Formation through C_sp²-C_sp² and P-H Bond Cleavage: Access to β-Ketophosphonates

J Org Chem. 2017 Dec 15;82(24):13268-13276. doi: 10.1021/acs.joc.7b02391. Epub 2017 Nov 22.

Authors

Pan Zhou¹, Biao Hu¹, Lingdan Li¹, Kairui Rao¹, Jiao Yang¹, Fuchao Yu¹

Affiliation

¹ Faculty of Life Science and Technology, Kunming University of Science and Technology , Kunming, 650500, P. R. China.

PMID: 29136376
DOI: 10.1021/acs.joc.7b02391

Abstract

The Mn(OAc)₃-promoted oxidative phosphonylation of N,N-dimethylenaminones with H-phosphonates, involving a chemo- and regioselective C_sp²-C_sp² bond cleavage and C_sp³-P bond formation in one step, provided successfully functionalized β-ketophosphonates under mild reaction conditions. Oxidative C_sp³-H/P-H cross-coupling reactions via C_sp³-C(C═O) bond cleavage and mechanistic studies are conducted preliminarily, and a possible mechanism is proposed. This novel method proceeds in good to excellent yields, shows operational simplicity, broad substrate scope, and large-scale preparation.

Publication types

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