Sharma, Sumeet K., Bishopp, Simon D., Liana Allen, C., Lawrence, R. (Ruth), Bamford, Mark J., Lapkin, Alexei, Plucinski, Pawel K., Watson, Robert J. and Williams, Jonathan M. J. (2011) Copper-catalyzed rearrangement of oximes into primary amides. Tetrahedron Letters, Vol.52 (No.33). pp. 4252-4255. doi:10.1016/j.tetlet.2011.05.129

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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.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry T Technology > TP Chemical technology
Divisions:	Faculty of Science > Engineering
Library of Congress Subject Headings (LCSH):	Amides, Oximes, Copper, Copper salts, Rearrangements (Chemistry), Metal catalysts
Journal or Publication Title:	Tetrahedron Letters
Publisher:	Pergamon
ISSN:	0040-4039
Official Date:	17 August 2011
Dates:	Date Event 17 August 2011 Published
Volume:	Vol.52
Number:	No.33
Number of Pages:	4
Page Range:	pp. 4252-4255
DOI:	10.1016/j.tetlet.2011.05.129
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
Funder:	Engineering and Physical Sciences Research Council (EPSRC), GlaxoSmithKline (GSK)
Grant number:	EP/G028141/1 (EPSRC)

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