Copper-catalyzed rearrangement of oximes into primary amides

Sumeet Kumar Sharma, Simon D Bishopp, C L Allen, R Lawrence, M J Bamford, A A Lapkin, Pawel Plucinski, R J Watson, Jonathan M J Williams

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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.
Original languageEnglish
Pages (from-to)4252-4255
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number33
DOIs
Publication statusPublished - 17 Aug 2011

Keywords

  • sustainable chemistry
  • amide
  • copper
  • synthetic methods
  • rearrangement

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    Sharma, S. K., Bishopp, S. D., Allen, C. L., Lawrence, R., Bamford, M. J., Lapkin, A. A., Plucinski, P., Watson, R. J., & Williams, J. M. J. (2011). Copper-catalyzed rearrangement of oximes into primary amides. Tetrahedron Letters, 52(33), 4252-4255. https://doi.org/10.1016/j.tetlet.2011.05.129