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Copper-catalyzed rearrangement of oximes into primary amides
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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 ISSN 0040-4039.
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Official URL: http://dx.doi.org/10.1016/j.tetlet.2011.05.129
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 |
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| Divisions: | Faculty of Science, Engineering and Medicine > Engineering > 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: |
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| 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) |
Data sourced from Thomson Reuters' Web of Knowledge
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