Mechanism of the ligand-free CuI-catalyzed azide-alkyne cycloaddition reaction

被引:557
作者
Rodionov, VO [1 ]
Fokin, VV [1 ]
Finn, MG [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
关键词
alkynes; azides; click chemistry; copper; cycloaddition;
D O I
10.1002/anie.200461496
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A powerful engine: The Cu-catalyzed azide-alkyne cycloaddition depends on rapid formation of CuI- acetylide complexes from terminal alkynes 2 and their ability to activate organic azides 1. A kinetics study uncovered a bimolecular dependence on the metal and an unusually fast intramolecular variant of the process. The results suggest the importance of 3 as a reactive intermediate. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
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页码:2210 / 2215
页数:6
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