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

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. Ox...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 82; no. 24; pp. 13268 - 13276
Main Authors Zhou, Pan, Hu, Biao, Li, Lingdan, Rao, Kairui, Yang, Jiao, Yu, Fuchao
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 15.12.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIRECT OXYPHOSPHORYLATION
KETO PHOSPHONATES
ENAMINONES
C-C
HETEROCYCLIC KETENE AMINALS
EFFICIENT CONSTRUCTION
DEHYDROGENATIVE COUPLING REACTION
DERIVATIVES
DYNAMIC KINETIC RESOLUTION
CASCADE REACTION
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Summary: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.
ISSN:0022-3263
DOI:10.1021/acs.joc.7b02391