Apparent Copper(II)-Accelerated Azide-Alkyne Cycloaddition

被引：207

作者：

Brotherton, Wendy S. ^{[1
]}

Michaels, Heather A. ^{[1
]}

Simmons, J. Tyler ^{[1
]}

Clark, Ronald J. ^{[1
]}

Dalal, Naresh S. ^{[1
]}

Zhu, Lei ^{[1
]}

机构：

[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 21期

基金：

美国国家科学基金会;

关键词：

DIVERSITY-ORIENTED SYNTHESIS; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; COPPER(II) COMPLEXES; CRYSTAL-STRUCTURE; METAL-COMPLEXES; ORGANIC AZIDES; LIGAND-FREE; CATALYST;

D O I：

10.1021/ol9021113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cu(II) salts accelerate azide-alkyne cycloaddition reactions in alcoholic solvents without reductants such as sodium ascorbate. Spectroscopic observations suggest that Cu(II) undergoes reduction to catalytic Cu(l) species via either alcohol oxidation or alkyne homocoupling, or both, during an induction period. The reactions involving 2-picolylazide are likely facilitated by its chelation to Cu(II). The highly exothermic reaction between 2-picolylazide and propargyl alcohol completes within 1-2 min in the presence of as low as 1 mol % Cu(OAC)(2).

引用

页码：4954 / 4957

页数：4