Copper-catalyzed rearrangement of oximes into primary amides
Sharma, S. K., Bishopp, S. D., Allen, C. L., Lawrence, R., Bamford, M. J., Lapkin, A. A., Plucinski, P., Watson, R. J. and Williams, J. M. J., 2011. Copper-catalyzed rearrangement of oximes into primary amides. Tetrahedron Letters, 52 (33), pp. 4252-4255.
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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.
|Creators||Sharma, S. K., Bishopp, S. D., Allen, C. L., Lawrence, R., Bamford, M. J., Lapkin, A. A., Plucinski, P., Watson, R. J. and Williams, J. M. J.|
|Uncontrolled Keywords||sustainable chemistry, amide, copper, synthetic methods, rearrangement|
|Departments||Faculty of Engineering & Design > Chemical Engineering|
Faculty of Science > Chemistry
|Publisher Statement||Williams_Tetrahedron-Letters_2011_52_33_4252.pdf: NOTICE: this is the author’s version of a work that was accepted for publication in . A definitive version was subsequently published in Tetrahedron Letters, [52, 33, (2011)] DOI: 10.1016/j.tetlet.2011.05.129|
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