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

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Oximes
Amides
Copper
Salts
Microwave heating
Precious metals
Microwaves
Activated carbon
Heating
Carbon
Metals
Costs and Cost Analysis
Atoms
Catalysts
Costs

Keywords

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

Cite this

Sharma, S. K., Bishopp, S. D., Allen, C. L., Lawrence, R., Bamford, M. J., Lapkin, A. A., ... 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

Copper-catalyzed rearrangement of oximes into primary amides. / Sharma, Sumeet Kumar; Bishopp, Simon D; Allen, C L; Lawrence, R; Bamford, M J; Lapkin, A A; Plucinski, Pawel; Watson, R J; Williams, Jonathan M J.

In: Tetrahedron Letters, Vol. 52, No. 33, 17.08.2011, p. 4252-4255.

Research output: Contribution to journalArticle

Sharma, SK, Bishopp, SD, Allen, CL, Lawrence, R, Bamford, MJ, Lapkin, AA, Plucinski, P, Watson, RJ & Williams, JMJ 2011, 'Copper-catalyzed rearrangement of oximes into primary amides', Tetrahedron Letters, vol. 52, no. 33, pp. 4252-4255. https://doi.org/10.1016/j.tetlet.2011.05.129
Sharma SK, Bishopp SD, Allen CL, Lawrence R, Bamford MJ, Lapkin AA et al. Copper-catalyzed rearrangement of oximes into primary amides. Tetrahedron Letters. 2011 Aug 17;52(33):4252-4255. https://doi.org/10.1016/j.tetlet.2011.05.129
Sharma, Sumeet Kumar ; Bishopp, Simon D ; Allen, C L ; Lawrence, R ; Bamford, M J ; Lapkin, A A ; Plucinski, Pawel ; Watson, R J ; Williams, Jonathan M J. / Copper-catalyzed rearrangement of oximes into primary amides. In: Tetrahedron Letters. 2011 ; Vol. 52, No. 33. pp. 4252-4255.
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