Mechanistic Insights into the One-Pot Synthesis of Propargylamines from Terminal Alkynes and Amines in Chlorinated Solvents Catalyzed by Gold Compounds and Nanoparticles

被引：65

作者：

Aguilar, David ^{[3
]}

Contel, Maria ^{[1
,2
]}

Urriolabeitia, Esteban P. ^{[3
]}

机构：

[1] CUNY, Brooklyn Coll, Dept Chem, Brooklyn, NY 11210 USA

[2] CUNY, Grad Ctr, Brooklyn, NY 11210 USA

[3] Univ Zaragoza, CSIC, Inst Ciencia Mat Aragon, Dept Compuestos Organometal, E-50009 Zaragoza, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 30期

关键词：

alkynes; C-C coupling; C-Cl activation; catalysis; gold; 3-COMPONENT COUPLING REACTION; DICHLOROMETHANE ACTIVATION; IMINOPHOSPHORANE COMPLEXES; BOND ACTIVATION; DIRECT-ADDITION; ALDEHYDE; COPPER; SILVER; 2,3,4,5-TETRAHYDROPYRIDINES; 5-ALKYNYLAMINES;

D O I：

10.1002/chem.201000587

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Propargylamines can be obtained from secondary amines and terminal alkynes in chlorinated solvents by a three- and two-component synthesis catalyzed by gold compounds and nanoparticles (Au-NP) under mild conditions. The use of dichloromethane allows for the activation of two C-Cl bonds and a clean transfer of the methylene fragment to the final product. The scope of the reaction as well as the influence of different gold(III) cycloaurated complexes and salts has been investigated. The involvement of gold nanoparticles generated in situ in the process is discussed and a plausible reaction mechanism is proposed on the basis of the data obtained.

引用

页码：9287 / 9296

页数：10

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