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金纳米粒子催化的炔丙胺合成:作为两步流动过程进行的传统 A3 多组分反应。

Gold-nanoparticle-catalyzed synthesis of propargylamines: the traditional A3-multicomponent reaction performed as a two-step flow process.

机构信息

Institute for Micro- and Nanotechnology, Department of Physical Chemistry and Micro Reaction Technology, Ilmenau University of Technology, Weimarerstrasse 32, 98693 Ilmenau, Germany.

出版信息

Chemistry. 2011 Mar 1;17(10):3005-10. doi: 10.1002/chem.201002043. Epub 2011 Jan 31.

DOI:10.1002/chem.201002043
PMID:21284044
Abstract

The alkyne, aldehyde, amine A(3)-coupling reaction, a traditional multicomponent reaction (MCR), has been investigated as a two-step flow process. The implicated aminoalkylation reaction of phenylacetylene with appropriate aldimine intermediates was catalyzed by gold nanoparticles impregnated on alumina. The aldimine formation was catalyzed by Montmorillonite K10 beforehand. The performance of the process has been investigated with respect to different reaction regimes. Usually, the A(3)-multicomponent reaction is performed as a "one-pot" process. Diversity-oriented syntheses using MCRs often have the shortcoming that only low selectivity and low yields are achieved. We have used a flow-chemistry approach to perform the A(3)-MCR in a sequential manner. In this way, the reaction performance was significantly enhanced in terms of shortened reaction time, and the desired propargylamines were obtained in high yields.

摘要

炔、醛、胺 A(3)-偶联反应是一种传统的多组分反应 (MCR),已被研究为两步流动过程。所涉及的炔与适当的亚胺中间体的氨基烷基化反应由负载在氧化铝上的金纳米粒子催化。亚胺的形成由蒙脱土 K10 预先催化。已经针对不同的反应条件研究了该过程的性能。通常,A(3)-多组分反应作为“一锅法”进行。使用多组分反应进行多样性导向合成的缺点通常是只能实现低选择性和低收率。我们使用流动化学方法以顺序方式进行 A(3)-MCR。通过这种方式,反应性能在缩短反应时间方面得到了显著提高,并且以高产率获得了所需的炔丙胺。

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