CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective

被引:1500
作者
Bock, VD [1 ]
Hiemstra, H [1 ]
van Maarseveen, JH [1 ]
机构
[1] Univ Amsterdam, Vant Hoff Inst Mol Sci, NL-1018 WS Amsterdam, Netherlands
关键词
click chemistry; cycloaddition; heterocycles; molecular diversity; azides;
D O I
10.1002/ejoc.200500483
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cu-I-catalyzed alkyne-azide cycloaddition provides 1,4-disubstituted 1,2,3-triazoles with such efficiency and scope that the transformation has been described as "click" chemistry. An overview of the mechanism of this remarkable reaction is presented as a means to explain the myriad of experimental results, particularly the various methods of catalyst generation, solvent and substrate effects, and choice of base or ligand. Both solution-phase and solid-phase results are comprehensively examined. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).
引用
收藏
页码:51 / 68
页数:18
相关论文
共 120 条
[1]   A versatile synthesis of fused triazolo derivatives by sequential Ugi/alkyne-azide cycloaddition reactions [J].
Akritopoulou-Zanze, I ;
Gracias, V ;
Djuric, SW .
TETRAHEDRON LETTERS, 2004, 45 (46) :8439-8441
[2]   1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY [J].
ALVAREZ, R ;
VELAZQUEZ, S ;
SANFELIX, A ;
AQUARO, S ;
DECLERCQ, E ;
PERNO, CF ;
KARLSSON, A ;
BALZARINI, J ;
CAMARASA, MJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) :4185-4194
[3]  
[Anonymous], MICROWAVES ORGANIC S
[4]   A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction [J].
Appukkuttan, P ;
Dehaen, W ;
Fokin, VV ;
Van der Eycken, E .
ORGANIC LETTERS, 2004, 6 (23) :4223-4225
[5]   Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine [J].
Bae, I ;
Han, H ;
Chang, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2038-2039
[6]  
BASTIDE J, 1973, B SOC CHIM FR II-CH, P2294
[7]  
Bastide J., 1978, CHEM CARBON CARBON T, P447
[8]   Parallel synthesis and biological screening of dopamine receptor ligands taking advantage of a click chemistry based BAL linker [J].
Bettinetti, L ;
Löber, S ;
Hübner, H ;
Gmeiner, P .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (02) :309-316
[9]   Synthesis of readily modifiable cyclodextrin analogues via cyclodimerization of an alkynyl-azido trisaccharide [J].
Bodine, KD ;
Gin, DY ;
Gin, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) :1638-1639
[10]  
Bohacek RS, 1996, MED RES REV, V16, P3, DOI 10.1002/(SICI)1098-1128(199601)16:1<3::AID-MED1>3.3.CO