Oxidative CO Cross‐Coupling of 1, 3‐Dicarbonyl Compounds and Their Heteroanalogues with N‐Substituted Hydroxamic Acids and N‐Hydroxyimides. Issue 11 (12th August 2013)

• Record Type: Journal Article
• Authors: Terent'ev, Alexander O.; Krylov, Igor B.; Timofeev, Vladimir P.; Starikova, Zoya A.; Merkulova, Valentina M.; Ilovaisky, Alexey I.; Nikishin, Gennady I.
• Is Part Of: Advanced synthesis & catalysis. Volume 355:Issue 11/12(2013)
• Page Start: 2375
• Page End: 2390
• Publication Date: 2013-08-12
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201300341
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The oxidative CO cross‐coupling of 1, 3‐dicarbonyl compounds and their heteroanalogues, 2‐substituted malononitriles and cyanoacetic esters, with <italic>N</italic>‐substituted hydroxamic acids and <italic>N</italic>‐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 [KMnO₄] system as the oxidant. The synthesis can be scaled up to gram quantities of coupling products; yields are 30–94%. The reaction proceeds <italic>via</italic> a radical mechanism through the formation of nitroxyl radicals from <italic>N</italic>‐substituted hydroxamic acids and <italic>N</italic>‐hydroxyimides.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg36h128dp" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>