Mechanistic Insights into Copper(I)-Catalyzed Azide-Alkyne Cycloadditions using Continuous Flow Conditions

被引：113

作者：

Fuchs, Michael ^{[1
,2
]}

Goessler, Walter ^{[2
]}

Pilger, Christian ^{[3
]}

Kappe, C. Oliver ^{[1
,2
]}

机构：

[1] Karl Franzens Univ Graz, CDLMC, A-8010 Graz, Austria

[2] Karl Franzens Univ Graz, Inst Chem, A-8010 Graz, Austria

[3] BASF SE, D-67056 Ludwigshafen, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 2-3期

关键词：

1,3-dipolar cycloaddition; click chemistry; copper catalysis; flow chemistry; microwave chemistry; 1,2,3-triazoles; ONE-POT SYNTHESIS; CLICK CHEMISTRY; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; TERMINAL ALKYNES; ARYL HALIDES; COPPER; COMPLEXES; OXIDATION; REACTORS; LIGANDS;

D O I：

10.1002/adsc.200900726

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The copper-catalyzed azide-alkyne cycloaddition (CuAAC, "click chemistry") was studied employing copper-in-charcoal (Cu/C) and a variety of copper metal sources as "heterogeneous" catalysts. The type and pretreatment conditions of the different copper sources oil the CuAAC were investigated. In addition, the effect of copper leaching from the catalyst over time and in dependence on the reaction mixture composition was studied by ICP-MS analysis in the continuous flow mode. These investigations confirm a "homogeneous" mechanism and suggest Surface layer copper(I) oxide as the catalytically active species in CUAAC chemistry involving zerovalent copper metal.

引用

页码：323 / 328

页数：6

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