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

Eva Havránková; Patrik Pospíšil; Pavel Pazdera

doi:doi:10.11648/j.sjc.s.2014020601.11

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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

Eva Havránková, Patrik Pospíšil, Pavel Pazdera

Published in Science Journal of Chemistry (Volume 2, Issue 6-1)

Received: 26 August 2014 Accepted: 6 September 2014 Published: 17 September 2014

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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.

Published in	Science Journal of Chemistry (Volume 2, Issue 6-1) This article belongs to the Special Issue Green Chemistry: Synthesis and Its Uses
DOI	10.11648/j.sjc.s.2014020601.11
Page(s)	1-8
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2014. Published by Science Publishing Group

Keywords

Imines, Metal Catalysis, Organocatalysis, Synergism, Polymer Supported Ce(III)

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Eva Havránková, Patrik Pospíšil, Pavel Pazdera. (2014). 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, 2(6-1), 1-8. https://doi.org/10.11648/j.sjc.s.2014020601.11

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ACS Style

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. Sci. J. Chem. 2014, 2(6-1), 1-8. doi: 10.11648/j.sjc.s.2014020601.11

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AMA Style

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. Sci J Chem. 2014;2(6-1):1-8. doi: 10.11648/j.sjc.s.2014020601.11

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@article{10.11648/j.sjc.s.2014020601.11,
  author = {Eva Havránková and Patrik Pospíšil and Pavel Pazdera},
  title = {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},
  journal = {Science Journal of Chemistry},
  volume = {2},
  number = {6-1},
  pages = {1-8},
  doi = {10.11648/j.sjc.s.2014020601.11},
  url = {https://doi.org/10.11648/j.sjc.s.2014020601.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.s.2014020601.11},
  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.},
 year = {2014}
}

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TY  - JOUR
T1  - 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
AU  - Eva Havránková
AU  - Patrik Pospíšil
AU  - Pavel Pazdera
Y1  - 2014/09/17
PY  - 2014
N1  - https://doi.org/10.11648/j.sjc.s.2014020601.11
DO  - 10.11648/j.sjc.s.2014020601.11
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 1
EP  - 8
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.s.2014020601.11
AB  - 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.
VL  - 2
IS  - 6-1
ER  -

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Author Information

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
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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Eva Havránková, Patrik Pospíšil, Pavel Pazdera. (2014). 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, 2(6-1), 1-8. https://doi.org/10.11648/j.sjc.s.2014020601.11

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ACS Style

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. Sci. J. Chem. 2014, 2(6-1), 1-8. doi: 10.11648/j.sjc.s.2014020601.11

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AMA Style

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. Sci J Chem. 2014;2(6-1):1-8. doi: 10.11648/j.sjc.s.2014020601.11

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@article{10.11648/j.sjc.s.2014020601.11,
  author = {Eva Havránková and Patrik Pospíšil and Pavel Pazdera},
  title = {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},
  journal = {Science Journal of Chemistry},
  volume = {2},
  number = {6-1},
  pages = {1-8},
  doi = {10.11648/j.sjc.s.2014020601.11},
  url = {https://doi.org/10.11648/j.sjc.s.2014020601.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.s.2014020601.11},
  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.},
 year = {2014}
}

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TY  - JOUR
T1  - 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
AU  - Eva Havránková
AU  - Patrik Pospíšil
AU  - Pavel Pazdera
Y1  - 2014/09/17
PY  - 2014
N1  - https://doi.org/10.11648/j.sjc.s.2014020601.11
DO  - 10.11648/j.sjc.s.2014020601.11
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 1
EP  - 8
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.s.2014020601.11
AB  - 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.
VL  - 2
IS  - 6-1
ER  -

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