Catalytic Acylation of Amines with Aldehydes or Aldoximes

被引:111
作者
Allen, C. Liana [1 ]
Davulcu, Simge [1 ]
Williams, Jonathan M. J. [1 ]
机构
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
基金
英国工程与自然科学研究理事会;
关键词
ONE-POT CONVERSION; ONE-STEP SYNTHESIS; OXIDATIVE AMIDATION; HIGHLY EFFICIENT; MILD AMIDATION; PRIMARY AMIDES; NITRILES; REARRANGEMENT; LANTHANIDE; COMPLEXES;
D O I
10.1021/ol101978h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The simple nickel salt NiCl2 center dot 6H(2)O catalyzes the coupling of aldoximes with amines to give secondary or tertiary amide products. The aldoxime can be prepared in situ from the corresponding aldehyde. The use of O-18-labeled oximes has allowed insight into the mechanism of this reaction.
引用
收藏
页码:5096 / 5099
页数:4
相关论文
共 42 条
[1]   Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature [J].
Al-Zoubi, Raed M. ;
Marion, Olivier ;
Hall, Dennis G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) :2876-2879
[2]   Palladium-Catalyzed One-Pot Conversion of Aldehydes to Amides [J].
Ali, Md Ashif ;
Punniyamurthy, Tharmalingam .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) :288-292
[3]   Cost efficient synthesis of amides from oximes with indium or zinc catalysts [J].
Allen, C. Liana ;
Burel, Celine ;
Williams, Jonathan M. J. .
TETRAHEDRON LETTERS, 2010, 51 (20) :2724-2726
[4]   An iron-catalysed synthesis of amides from nitriles and amines [J].
Allen, C. Liana ;
Lapkin, Alexei A. ;
Williams, Jonathan M. J. .
TETRAHEDRON LETTERS, 2009, 50 (29) :4262-4264
[5]   N-heterocyclic carbene-catalyzed redox amidations of α-functionalized aldehydes with amines [J].
Bode, Jeffrey W. ;
Sohn, Stephanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13798-+
[6]   Analysis of the reactions used for the preparation of drug candidate molecules [J].
Carey, John S. ;
Laffan, David ;
Thomson, Colin ;
Williams, Mike T. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347
[7]   Rh(II)-Catalyzed intermolecular oxidative sulfamidation of aldehydes:: A mild efficient synthesis of N-sulfonylcarboxamides [J].
Chan, Johann ;
Baucorn, Kyle D. ;
Murry, Jerry A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) :14106-+
[8]   Platinum catalysed hydrolytic amidation of unactivated nitriles [J].
Cobley, CJ ;
van den Heuvel, M ;
Abbadi, A ;
de Vries, JG .
TETRAHEDRON LETTERS, 2000, 41 (14) :2467-2470
[9]   Key green chemistry research areas - a perspective from pharmaceutical manufacturers [J].
Constable, David J. C. ;
Dunn, Peter J. ;
Hayler, John D. ;
Humphrey, Guy R. ;
Leazer, Johnnie L., Jr. ;
Linderman, Russell J. ;
Lorenz, Kurt ;
Manley, Julie ;
Pearlman, Bruce A. ;
Wells, Andrew ;
Zaks, Aleksey ;
Zhang, Tony Y. .
GREEN CHEMISTRY, 2007, 9 (05) :411-420
[10]   Metal-free one-pot oxidative amination of aldehydes to amides [J].
Ekoue-Kovi, Kekeli ;
Wolf, Christian .
ORGANIC LETTERS, 2007, 9 (17) :3429-3432