Gold-Nanoparticle-Catalyzed Synthesis of Propargylamines: The Traditional A3-Multicomponent Reaction Performed as a Two-Step Flow Process

被引:53
作者
Abahmane, Lahbib [1 ]
Koehler, J. Michael [1 ]
Gross, G. Alexander [1 ]
机构
[1] Ilmenau Univ Technol, Inst Micro & Nanotechnol, Dept Phys Chem & Micro React Technol, D-98693 Ilmenau, Germany
关键词
flow chemistry; gold; multicomponent reactions; nanoparticles; packed-bed capillary reactor; propargylamines; 3-COMPONENT COUPLING REACTION; MULTICOMPONENT REACTIONS; ALDEHYDE; ALKYNE; MICROREACTOR; CHEMISTRY; REACTORS; AMINES; ALKYNYLATION; GENERATION;
D O I
10.1002/chem.201002043
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:3005 / 3010
页数:6
相关论文
共 64 条
[1]   Synthesis of polypyridine derivatives using alumina supported gold nanoparticles under micro continuous flow conditions [J].
Abahmane, Lahbib ;
Knauer, Andrea ;
Koehler, J. Michael ;
Gross, G. Alexander .
CHEMICAL ENGINEERING JOURNAL, 2011, 167 (2-3) :519-526
[2]   Heterogeneous Catalyzed Pyridine Synthesis using Montmorillionite and Nanoparticle-Impregnated Alumina in a Continuous Micro Flow System [J].
Abahmane, Lahbib ;
Knauer, Andrea ;
Ritter, Uwe ;
Koehler, J. Michael ;
Gross, G. Alexander .
CHEMICAL ENGINEERING & TECHNOLOGY, 2009, 32 (11) :1799-1805
[3]   A HCN-based reaction under microreactor conditions:: industrially feasible and continuous synthesis of 3,4-diamino-1H-isochromen-1-ones [J].
Acke, Davy R. J. ;
Stevens, Christian V. .
GREEN CHEMISTRY, 2007, 9 (04) :386-390
[4]  
[Anonymous], ANGEW CHEM
[5]  
[Anonymous], 2000, ANGEW CHEM
[6]  
Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
[7]  
2-E
[8]  
Arend M., 1998, ANGEW CHEM, V110, P1096, DOI DOI 10.1002/(SICI)1521-3757(19980420)110:8
[9]   Montmorillonite K-10: As a Useful Catalyst in Organic Preparations [J].
Baghernejad, Bita .
LETTERS IN ORGANIC CHEMISTRY, 2010, 7 (03) :255-268
[10]   Diversity-Oriented Synthesis of Dibenzoazocines and Dibenzoazepines via a Microwave-Assisted Intramolecular A3-Coupling Reaction [J].
Bariwal, Jitender B. ;
Ermolat'ev, Denis S. ;
Glasnov, Toma N. ;
Van Hecke, Kristof ;
Mehta, Vaibhav P. ;
Van Meervelt, Luc ;
Kappe, C. Oliver ;
Van der Eycken, Erik V. .
ORGANIC LETTERS, 2010, 12 (12) :2774-2777