Copper-catalyzed rearrangement of oximes into primary amides

被引：68

作者：

Sharma, Sumeet K. ^{[1
,4
]}

Bishopp, Simon D. ^{[1
]}

Allen, C. Liana ^{[1
]}

Lawrence, Ruth ^{[1
]}

Bamford, Mark J. ^{[2
]}

Lapkin, Alexei A. ^{[3
]}

Plucinski, Pawel ^{[4
]}

Watson, Robert J. ^{[2
]}

Williams, Jonathan M. J. ^{[1
]}

机构：

[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England

[2] GlaxoSmithKline Res & Dev Ltd, Stevenage SG1 2NY, Herts, England

[3] Univ Warwick, Sch Engn, Coventry CV4 7AL, W Midlands, England

[4] Univ Bath, Dept Chem Engn, Bath BA2 7AY, Avon, England

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 33期

基金：

英国工程与自然科学研究理事会;

关键词：

Amide; Copper; Rearrangement; Sustainable chemistry; Synthetic methods; ONE-POT CONVERSION; ALDOXIMES; ALDEHYDES;

D O I：

10.1016/j.tetlet.2011.05.129

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：4252 / 4255

页数：4

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