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

The Mn­(OAc)3-promoted oxidative phosphonylation of N,N-dimethylenaminones with H-phosphonates, involving a chemo- and regioselective Csp2 –Csp2 bond cleavage and Csp3 –P bond formation in one step, provided successfully functionalized β-ketophosphonates under mild reaction conditions. Oxidative Csp...

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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 American Chemical Society 15.12.2017
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Summary:The Mn­(OAc)3-promoted oxidative phosphonylation of N,N-dimethylenaminones with H-phosphonates, involving a chemo- and regioselective Csp2 –Csp2 bond cleavage and Csp3 –P bond formation in one step, provided successfully functionalized β-ketophosphonates under mild reaction conditions. Oxidative Csp3 –H/P–H cross-coupling reactions via Csp3 –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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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02391