4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 24, Pages 13268-13276

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02391

Keywords

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Funding

  1. National Natural Science Foundation of China [21402070]
  2. Analytical & Testing Foundation of Kunming University of Science and Technology [2017T20130137, 2017M20152118097, 2017M20162218006]

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The Mn(OAc)(3)-promoted oxidative phosphonylation of N,N-dimethylenaminones with H-phosphonates, involving a chemo- and regioselective C-sp(2)-C-sp(2) bond cleavage and C-sp(3)-P bond formation in one step, provided successfully functionalized beta-ketophosphonates under mild reaction conditions. Oxidative C-sp(3)-H/P H cross-coupling reactions via C-sp(3)-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.

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