Synergism of Metal and Organocatalysis in Condensation Reactions of Aromatic Aldehydes with Anilines Affording Imines: Effect of Catalysts on the Base of a Supported Cerium(III) and Proline
Science Journal of Chemistry
Volume 2, Issue 6-1, December 2014, Pages: 1-8
Received: Aug. 26, 2014; Accepted: Sep. 6, 2014; Published: Sep. 17, 2014
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Authors
Eva Havránková, Centre for Syntheses at Sustainable Conditions and their Management, Chemistry Department, Masaryk University, Kamenice 5, CZ-625 00 Brno, Czech Republic
Patrik Pospíšil, Gymnázium Brno, Kpt. Jaroše 14, CZ-658 70, Brno 2, Czech Republic
Pavel Pazdera, Centre for Syntheses at Sustainable Conditions and their Management, Chemistry Department, Masaryk University, Kamenice 5, CZ-625 00 Brno, Czech Republic
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Abstract
Condensation reactions between 4-X-benzaldehydes (X = NO2, H, OCH3) and 4-Y-anilines (X = NO2, H, OCH3) catalyzed by new catalyst, i.e. Ce (III) supported on weakly acidic cation-exchanger resin of polyacrylate type and/or by proline as organocatalyst giving 4-Y-N-[(E)-(4-X-phenyl)methylidene]anilines, were studied. It was found that the both of the used catalysts, i.e. metal and organocatalyst, shortened reaction time, thus contributing to higher yields of products. The synergism between catalytic action of polymer supported Ce (III) and proline was found. It was observed that simultaneous application of metal and organocatalyst led to shorter reaction times. On the other hand, it was found that the synergic efficiency of the both applied catalysts depends on electron influence of the substituents X, Y present in 4-X-benzaldehyde and 4-Y-aniline, as well. Imines were prepared under catalysis by Ce (III), proline or by simultaneous use of both catalysts in the yields 97-99% and identified. For comparison, the above mentioned condensation reactions were carried out under classical catalysis by mineral acid with different, usually poor, results.
Keywords
Imines, Metal Catalysis, Organocatalysis, Synergism, Polymer Supported Ce(III)
To cite this article
Eva Havránková, Patrik Pospíšil, Pavel Pazdera, Synergism of Metal and Organocatalysis in Condensation Reactions of Aromatic Aldehydes with Anilines Affording Imines: Effect of Catalysts on the Base of a Supported Cerium(III) and Proline, Science Journal of Chemistry. Special Issue: Green Chemistry: Synthesis and Its Uses. Vol. 2, No. 6-1, 2014, pp. 1-8. doi: 10.11648/j.sjc.s.2014020601.11
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