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Gold‐Nanoparticle‐Catalyzed Synthesis of Propargylamines: The Traditional A 3 ‐Multicomponent Reaction Performed as a Two‐Step Flow Process
Author(s) -
Abahmane Lahbib,
Köhler J. Michael,
Groß G. Alexander
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002043
Subject(s) - phenylacetylene , aldimine , catalysis , flow chemistry , alkyne , chemistry , combinatorial chemistry , amine gas treating , selectivity , nanoparticle , coupling reaction , colloidal gold , aldehyde , reaction conditions , organic chemistry , materials science , nanotechnology
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.