Copper-catalyzed rearrangement of oximes into primary amides

Reference:

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.

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.

Details

Item Type	Articles
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.
DOI	10.1016/j.tetlet.2011.05.129
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
Refereed	Yes
Status	Published
ID Code	25474

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