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
相关论文
共 447 条
[101]   Efficient templated synthesis of donor - Acceptor rotaxanes using click chemistry [J].
Dichtel, William R. ;
Miljanic, Ognjen S. ;
Spruell, Jason M. ;
Heath, James R. ;
Stoddart, J. Fraser .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (32) :10388-10390
[102]   Preparation of biohybrid amphiphiles via the copper catalysed Huisgen [3+2] dipolar cycloaddition reaction [J].
Dirks, AJT ;
van Berkel, SS ;
Hatzakis, NS ;
Opsteen, JA ;
van Delft, FL ;
Cornelissen, JJLM ;
Rowan, AE ;
van Hest, JCM ;
Rutjes, FPJT ;
Nolte, RJM .
CHEMICAL COMMUNICATIONS, 2005, (33) :4172-4174
[103]   Modular synthesis of ChiraClick ligands: A library of P-chirogenic phosphines [J].
Dolhem, Franck ;
Johansson, Magnus J. ;
Antonsson, Thomas ;
Kann, Nina .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (03) :477-486
[104]   Assembling heterocycle-tethered C-glycosyl and α-amino acid residues via 1,3-dipolar cycloaddition reactions [J].
Dondoni, A ;
Giovannini, PP ;
Massi, A .
ORGANIC LETTERS, 2004, 6 (17) :2929-2932
[105]   Triazole: the keystone in glycosylated molecular architectures constructed by a click reaction [J].
Dondoni, Alessandro .
CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (06) :700-708
[106]   C-glycoside clustering on calix[4]arene, adamantane, and benzene scaffolds through 1,2,3-triazole linkers [J].
Dondoni, Alessandro ;
Marra, Alberto .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (20) :7546-7557
[107]  
Dong WL, 2006, CHINESE J ORG CHEM, V26, P271
[108]  
Dörner S, 2005, CHEM COMMUN, P2852, DOI 10.1039/b502682b
[109]   Protein semi-synthesis: New proteins for functional and structural studies [J].
Durek, T ;
Becker, CFW .
BIOMOLECULAR ENGINEERING, 2005, 22 (5-6) :153-172
[110]   One-pot synthesis of ABC type triblock copolymers via in situ click [3+2] and Diels-Alder [4+2] reactions [J].
Durmaz, Hakan ;
Dag, Aydan ;
Altintas, Ozcan ;
Erdogan, Tuba ;
Hizal, Gurkan ;
Tunca, Umit .
MACROMOLECULES, 2007, 40 (02) :191-198