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Oxidative CO Cross‐Coupling of 1,3‐Dicarbonyl Compounds and Their Heteroanalogues with N ‐Substituted Hydroxamic Acids and N ‐Hydroxyimides
Author(s) -
Terent'ev Alexander O.,
Krylov Igor B.,
Timofeev Vladimir P.,
Starikova Zoya A.,
Merkulova Valentina M.,
Ilovaisky Alexey I.,
Nikishin Gennady I.
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300341
Subject(s) - chemistry , potassium permanganate , cyanoacetic acid , manganese(iii) acetate , hydroxamic acid , manganese , catalysis , radical , medicinal chemistry , cobalt , oxidative coupling of methane , oxidative decarboxylation , organic chemistry
The oxidative CO cross‐coupling of 1,3‐dicarbonyl compounds and their heteroanalogues, 2‐substituted malononitriles and cyanoacetic esters, with N ‐substituted hydroxamic acids and N ‐hydroxyimides was realized. The best results were obtained with the use of manganese(III) acetate [Mn(OAc) 3 ] or the cobalt(II) acetate catalyst [Co(OAc) 2cat. ]/potassium permanganate [KMnO 4 ] system as the oxidant. The synthesis can be scaled up to gram quantities of coupling products; yields are 30–94%. The reaction proceeds via a radical mechanism through the formation of nitroxyl radicals from N ‐substituted hydroxamic acids and N ‐hydroxyimides.

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