Catalytic amide formation from non-activated carboxylic acids and amines

被引:594
作者
Lundberg, Helena [1 ]
Tinnis, Fredrik [1 ]
Selander, Nicklas [1 ]
Adolfsson, Hans [1 ]
机构
[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden
基金
瑞典研究理事会;
关键词
TERMINAL PEPTIDE AMIDATION; HIGHLY EFFICIENT SYNTHESIS; SOLID-PHASE SYNTHESIS; ONE-POT SYNTHESIS; N-FORMYLATION; BOND FORMATION; BORIC-ACID; 4-NITROBENZOIC ACID; ENZYMATIC-SYNTHESIS; ACETIC-ACID;
D O I
10.1039/c3cs60345h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The amide functionality is found in a wide variety of biological and synthetic structures such as proteins, polymers, pesticides and pharmaceuticals. Due to the fact that synthetic amides are still mainly produced by the aid of coupling reagents with poor atom-economy, the direct catalytic formation of amides from carboxylic acids and amines has become a field of emerging importance. A general, efficient and selective catalytic method for this transformation would meet well with the increasing demands for green chemistry procedures. This review covers catalytic and synthetically relevant methods for direct condensation of carboxylic acids and amines. A comprehensive overview of homogeneous and heterogeneous catalytic methods is presented, covering biocatalysts, Lewis acid catalysts based on boron and metals as well an assortment of other types of catalysts.
引用
收藏
页码:2714 / 2742
页数:29
相关论文
共 171 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]   Direct amide formation from unactivated carboxylic acids and amines [J].
Allen, C. Liana ;
Chhatwal, A. Rosie ;
Williams, Jonathan M. J. .
CHEMICAL COMMUNICATIONS, 2012, 48 (05) :666-668
[3]   Metal-catalysed approaches to amide bond formation [J].
Allen, C. Liana ;
Williams, Jonathan M. J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3405-3415
[4]   Size and Shape Control of Metal Nanoparticles for Reaction Selectivity in Catalysis [J].
An, Kwangjin ;
Somorjai, Gabor A. .
CHEMCATCHEM, 2012, 4 (10) :1512-1524
[5]   Silica supported perchloric acid catalyzed rapid N-formylation under solvent-free conditions [J].
Ansari, Mohd Imran ;
Hussain, Mohd Kamil ;
Yadav, Nisha ;
Gupta, Puneet K. ;
Hajela, K. .
TETRAHEDRON LETTERS, 2012, 53 (16) :2063-2065
[6]   Asymmetric direct amide synthesis by kinetic amine resolution:: A chiral bifunctional aminoboronic acid catalyzed reaction between a racemic amine and an achiral carboxylic acid [J].
Arnold, Kenny ;
Davies, Bryan ;
Herault, Damien ;
Whiting, Andrew .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (14) :2673-2676
[7]   Synthesis, evaluation and application of novel bifunctional N,N-di-isopropylbenzylamineboronic acid catalysts for direct amide formation between carboxylic acids and amines [J].
Arnold, Kenny ;
Batsanov, Andrei S. ;
Davies, Bryan ;
Whiting, Andrew .
GREEN CHEMISTRY, 2008, 10 (01) :124-134
[8]   To catalyze or not to catalyze? Insight into direct amide bond formation from amines and carboxylic acids under thermal and catalyzed conditions [J].
Arnold, Kenny ;
Davies, Bryan ;
Giles, Richard L. ;
Grosjean, Christophe ;
Smith, Gillian E. ;
Whiting, Andrew .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (7-8) :813-820
[9]   Deep eutectic solvent promoted highly efficient synthesis of N, N′-diarylamidines and formamides [J].
Azizi, Najmadin ;
Gholibeglo, Elham ;
Babapour, Mahbobe ;
Ghafuri, Hossein ;
Bolourtchian, Seyed Mohammad .
COMPTES RENDUS CHIMIE, 2012, 15 (09) :768-773
[10]   An Efficient Method for N-Formylation of Amines Using Natural HEU Zeolite at Room Temperature Under Solvent-Free Conditions [J].
Bahari, Siavash ;
Mohammadi-Aghdam, Babak ;
Sajadi, S. Mohammad ;
Zeidali, Fereshteh .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (07) :2251-2254