Cu-catalyzed azide-alkyne cycloaddition

被引:4150
作者
Meldal, Morten [1 ]
Tornoe, Christian Wenzel
机构
[1] Carlsberg Lab, DK-2500 Valby, Denmark
基金
新加坡国家研究基金会;
关键词
D O I
10.1021/cr0783479
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The copper catalysis in the Huisgen reaction broadly known as the azide/ alkyne reaction or CuAAC reaction has been discussed. This simple and robust reaction, which involves clusters of Cu and ligands, has led to exclusive formation of the 1,4-isomer. It is vital to maintain a good concentration of Cu throughout the reaction medium particularly in the case of less reactive reaction components or dilute reactions. The ligands' role in protecting the copper from oxidation or disproportionation is also important. The ligands also influence the structure and equilibria of copper clusters and may promote the formation of the most catalytically active copper complexes. The CuAAC reaction may be designed to accommodate all types of protecting groups and reactive intermediates.
引用
收藏
页码:2952 / 3015
页数:64
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共 447 条
[21]   Catalytic "click" rotaxanes:: A substoichiometric metal-template pathway to mechanically interlocked architectures [J].
Aucagne, V ;
Hänni, KD ;
Leigh, DA ;
Lusby, PJ ;
Walker, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2186-2187
[22]   Catalytic "Active-Metal" template synthesis of [2]rotaxanes, [3]rotaxanes, and molecular shuttles, and some observations on the mechanism of the Cu(I)-catalyzed azide-alkyne 1,3-cycloaddition [J].
Aucagne, Vincent ;
Berna, Jose ;
Crowley, James D. ;
Goldup, Stephen M. ;
Haenni, Kevin D. ;
Leigh, David A. ;
Lusby, Paul J. ;
Ronaldson, Vicki E. ;
Slawin, Alexandra M. Z. ;
Viterisi, Aurlien ;
Walker, D. Barney .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) :11950-11963
[23]   Chemoselective formation of successive triazole linkages in one pot: " Click-click" chemistry [J].
Aucagne, Vincent ;
Leigh, David A. .
ORGANIC LETTERS, 2006, 8 (20) :4505-4507
[24]   1,3-dipolar cycloaddition for the generation of nanostructured semiconductors by heated probe tips [J].
Bakbak, Selma ;
Leech, Peter J. ;
Carson, Bradley E. ;
Saxena, Shubham ;
King, William P. ;
Bunz, Uwe H. F. .
MACROMOLECULES, 2006, 39 (20) :6793-6795
[25]   A new chemical probe for proteomics of carbohydrate-binding proteins [J].
Ballell, L ;
Alink, KJ ;
Slijper, M ;
Versluis, C ;
Liskamp, RMJ ;
Pieters, RJ .
CHEMBIOCHEM, 2005, 6 (02) :291-295
[26]   A new chemical probe for the detection of the cancer-linked galectin-3 [J].
Ballell, Lluis ;
van Scherpenzeel, Monique ;
Buchalova, Katerina ;
Liskamp, Rob M. J. ;
Pieters, Roland J. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (23) :4387-4394
[27]   A cyclodextrin molecular reactor for the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles [J].
Barr, L ;
Lincoln, SF ;
Easton, CJ .
SUPRAMOLECULAR CHEMISTRY, 2005, 17 (07) :547-555
[28]   Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages [J].
Barral, Karine ;
Moorhouse, Adam D. ;
Moses, John E. .
ORGANIC LETTERS, 2007, 9 (09) :1809-1811
[29]   Copper-free click chemistry for dynamic in vivo imaging [J].
Baskin, Jeremy M. ;
Prescher, Jennifer A. ;
Laughlin, Scott T. ;
Agard, Nicholas J. ;
Chang, Pamela V. ;
Miller, Isaac A. ;
Lo, Anderson ;
Codelli, Julian A. ;
Bertozzi, Carolyn R. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) :16793-16797
[30]   Assessing the suitability of 1,2,3-triazole linkers for covalent immobilization of chiral ligands:: Application to enantioselective phenylation of aldehydes [J].
Bastero, Amaia ;
Font, Daniel ;
Pericas, Miquel A. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (07) :2460-2468