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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.

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    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
    CreatorsSharma, 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.
    DOI10.1016/j.tetlet.2011.05.129
    Uncontrolled Keywordssustainable chemistry, amide, copper, synthetic methods, rearrangement
    DepartmentsFaculty of Engineering & Design > Chemical Engineering
    Faculty of Science > Chemistry
    Publisher StatementWilliams_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
    RefereedYes
    StatusPublished
    ID Code25474

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