Metal-catalysed approaches to amide bond formation

被引:933
作者
Allen, C. Liana [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; CARBON-MONOXIDE; ARYL HALIDES; STEREOSELECTIVE-SYNTHESIS; CARBONYLATION REACTIONS; ATMOSPHERIC-PRESSURE; OXIDATIVE AMIDATION; SECONDARY AMIDES; VINYL HALIDES; N-FORMYLATION;
D O I
10.1039/c0cs00196a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Amongst the many ways of constructing the amide bond, there has been a growing interest in the use of metal-catalysed methods for preparing this important functional group. In this tutorial review, highlights of the recent literature have been presented covering the key areas where metal catalysts have been used in amide bond formation. Acids and esters have been used in coupling reactions with amines, but aldehydes and alcohols have also been used in oxidative couplings. The use of nitriles and oximes as starting materials for amide formation are also emerging areas of interest. The use of carbon monoxide in the transition metal catalysed coupling of amines has led to a powerful methodology for amide bond formation and this is complemented by the addition of an aryl or alkenyl group to an amide typically using palladium or copper catalysts.
引用
收藏
页码:3405 / 3415
页数:11
相关论文
共 76 条
[41]   Aminocarbonylation of phenylacetylene catalysed by palladium acetate in combination with (2-pyridyl)diphenylphosphine and methanesulfonic acid [J].
Matteoli, U ;
Scrivanti, A ;
Beghetto, V .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 213 (02) :183-186
[42]   Cobalt coordination induced functionalized molecular clefts:: Isolation of {CoIII-ZnII} heterometallic complexes and their applications in Beckmann rearrangement reactions [J].
Mishra, Anurag ;
Ali, Afsar ;
Upreti, Shailesh ;
Gupta, Rajeev .
INORGANIC CHEMISTRY, 2008, 47 (01) :154-161
[43]   PALLADIUM-CATALYZED CARBONYLATION OF ALLYLAMINES [J].
MURAHASHI, SI ;
IMADA, Y ;
NISHIMURA, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (24) :1578-1579
[44]   RUTHENIUM-CATALYZED AMIDATION OF NITRILES WITH AMINES - A NOVEL, FACILE ROUTE TO AMIDES AND POLYAMIDES [J].
MURAHASHI, SI ;
NAOTA, T ;
SAITO, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (24) :7846-7847
[45]  
NAOTA T, 1991, SYNLETT, P693
[46]   Amide Synthesis from Alcohols and Amines by the Extrusion of Dihydrogen [J].
Nordstrom, Lars Ulrik ;
Vogt, Henning ;
Madsen, Robert .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (52) :17672-+
[47]   Microwave-promoted aminocarbonylation of aryl triflates using Mo(CO)6 as a solid CO source [J].
Odell, Luke R. ;
Savmarker, Jonas ;
Larhed, Mats .
TETRAHEDRON LETTERS, 2008, 49 (42) :6115-6118
[48]   Preparation of benzolactams by Pd(OAc)2-catalyzed direct aromatic carbonylation [J].
Orito, K ;
Horibata, A ;
Nakamura, T ;
Ushito, H ;
Nagasaki, H ;
Yuguchi, M ;
Yamashita, S ;
Tokuda, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (44) :14342-14343
[49]   Highly efficient ruthenium-catalyzed oxime to amide rearrangement [J].
Owston, Nathan A. ;
Parker, Alexandra J. ;
Williams, Jonathan M. J. .
ORGANIC LETTERS, 2007, 9 (18) :3599-3601
[50]   Iridium-catalyzed conversion of alcohols into amides via oximes [J].
Owston, Nathan A. ;
Parker, Alexandra J. ;
Williams, Jonathan M. J. .
ORGANIC LETTERS, 2007, 9 (01) :73-75