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Copper-catalyzed rearrangement of oximes into primary amides
Authors:Sumeet K Sharma  Simon D BishoppC Liana Allen  Ruth LawrenceMark J Bamford  Alexei A LapkinPawel Plucinski  Robert J WatsonJonathan MJ Williams
Institution:a Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK
b GlaxoSmithKline Research and Development, Gunnels Wood Road, Stevenage SG1 2NY, UK
c School of Engineering, University of Warwick, Coventry CV4 7AL, UK
d Department of Chemical Engineering, University of Bath, Claverton Down, Bath BA2 7AY, UK
Abstract:The atom-efficient and cost-effective rearrangement of oximes into primary amides is catalyzed by simple copper salts. The use of homogeneous Cu(OAc)2 (1-2 mol %) was found to be effective for this transformation at 80 °C. The reaction was successful with either conventional or microwave heating. CuO and CuO/ZnO on activated carbon provided a competent reuseable heterogeneous catalyst which could be used in a batch process or in flow. Copper salts are much cheaper than the precious metals previously used for this rearrangement, and the reaction conditions are milder than those reported.
Keywords:Amide  Copper  Rearrangement  Sustainable chemistry  Synthetic methods
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