Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature

被引:361
作者
Al-Zoubi, Raed M. [1 ]
Marion, Olivier [1 ]
Hall, Dennis G. [1 ]
机构
[1] Univ Alberta, Dept Chem, Gunning Lemieux Chem Ctr, Edmonton, AB T6G 2G2, Canada
关键词
amides; boronic acids; carboxylic acids; cycloaddition; organocatalysis;
D O I
10.1002/anie.200705468
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Taming carboxylic acids: ortho-Iodo- and ortho-bromophenylboronic acids are exceptional organocatalysts in atom-economical amidations between free carboxylic acids and amines, including functionalized ones, and can also provide LUMO-lowering activation in [4 + 2] cycloadditions of α,β-unsaturated carboxylic acids. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2876 / 2879
页数:4
相关论文
共 29 条
[1]  
Anikina L. V., 2002, PHARM CHEM J, V36, P237
[2]   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
[3]   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
[4]   Iterative, aqueous synthesis of β3-oligopeptides without coupling reagents [J].
Carrillo, N ;
Davalos, EA ;
Russak, JA ;
Bode, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1452-1453
[5]   A CONVENIENT SYNTHESIS OF AMIDES FROM CARBOXYLIC-ACIDS AND PRIMARY AMINES [J].
COSSY, J ;
PALEGROSDEMANGE, C .
TETRAHEDRON LETTERS, 1989, 30 (21) :2771-2774
[6]   An improved class of sugar-binding boronic acids, soluble and capable of complexing glycosides in neutral water [J].
Dowlut, M ;
Hall, DG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (13) :4226-4227
[7]   Iminium catalysis [J].
Erkkila, Anniina ;
Majander, Inkeri ;
Pihko, Petri M. .
CHEMICAL REVIEWS, 2007, 107 (12) :5416-5470
[8]   ACYLOXYBORANE - AN ACTIVATING DEVICE FOR CARBOXYLIC-ACIDS [J].
FURUTA, K ;
MIWA, Y ;
IWANAGA, K ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6254-6255
[9]   A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases [J].
Ghose, AK ;
Viswanadhan, VN ;
Wendoloski, JJ .
JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (01) :55-68
[10]   Direct synthesis of amides from alcohols and amines with liberation of H2 [J].
Gunanathan, Chidambaram ;
Ben-David, Yehoshoa ;
Milstein, David .
SCIENCE, 2007, 317 (5839) :790-792