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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.
- sustainable chemistry
- synthetic methods
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