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

被引：560

作者：

Rodionov, VO ^{[1
]}

Fokin, VV ^{[1
]}

Finn, MG ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 15期

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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