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Asymmetric Intermolecular Heck Reaction of Aryl Halides by Pd-histidine Organocatalysts

Received: 20 April 2020     Accepted: 5 May 2020     Published: 28 June 2020
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Abstract

Extensive studies of asymmetric intermolecular Heck reaction are described and provide a deeper insight into histidine-catalyzed. In particular, aspects of enantio- as well as diastereoselectivity of these reactions are discussed. As the first report, we synthesized five histidine-based organocatalyts including histidine as a well-defined and biodegradable natural structure alone and in combination with 2,4,6-trichloro-1,3,5-triazine, benzene-1,3-diamine, dimethyl malonate and dimeric structure applied in the asymmetric intermolecular Heck reaction of aryl halides; their efficiency was compared to each other’s. These phosphine-free palladium catalysts were found as efficient catalytic system which provided the superior efficiency with excellent yields, regioselectivity and enantioselectivity. In these among, histidine with 2,4,6-trichloro-1,3,5-triazine which generate the star like molecule palladium catalyst gave the best activity in asymmetric intermolecular Heck reaction with excellent yields and good regio- and enantioselectivity under mild reaction conditions. The asymmetric intermolecular Heck reaction has been limited to aryl and vinyl triflates or aryl iodide in the rare reports of available Pd catalysts. Herein, we extend the reaction to aryl bromides. In addition, the scope of reaction was examined in two different techniques: conventional heating and microwave irradiation and compared. For the first time, microwave irradiation sintering is successfully used for this reaction. Comparison of catalytic activities of our catalyst (Pd/His) with literature examples confirmed our success.

Published in Modern Chemistry (Volume 8, Issue 2)
DOI 10.11648/j.mc.20200802.11
Page(s) 18-22
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), 2020. Published by Science Publishing Group

Keywords

Heck, Asymmetric Reaction, Palladium, Organocatalytst, Histidine

References
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  • APA Style

    Abdol Reza Hajipour, Zahra Khorsandi. (2020). Asymmetric Intermolecular Heck Reaction of Aryl Halides by Pd-histidine Organocatalysts. Modern Chemistry, 8(2), 18-22. https://doi.org/10.11648/j.mc.20200802.11

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    ACS Style

    Abdol Reza Hajipour; Zahra Khorsandi. Asymmetric Intermolecular Heck Reaction of Aryl Halides by Pd-histidine Organocatalysts. Mod. Chem. 2020, 8(2), 18-22. doi: 10.11648/j.mc.20200802.11

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    AMA Style

    Abdol Reza Hajipour, Zahra Khorsandi. Asymmetric Intermolecular Heck Reaction of Aryl Halides by Pd-histidine Organocatalysts. Mod Chem. 2020;8(2):18-22. doi: 10.11648/j.mc.20200802.11

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  • @article{10.11648/j.mc.20200802.11,
      author = {Abdol Reza Hajipour and Zahra Khorsandi},
      title = {Asymmetric Intermolecular Heck Reaction of Aryl Halides by Pd-histidine Organocatalysts},
      journal = {Modern Chemistry},
      volume = {8},
      number = {2},
      pages = {18-22},
      doi = {10.11648/j.mc.20200802.11},
      url = {https://doi.org/10.11648/j.mc.20200802.11},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20200802.11},
      abstract = {Extensive studies of asymmetric intermolecular Heck reaction are described and provide a deeper insight into histidine-catalyzed. In particular, aspects of enantio- as well as diastereoselectivity of these reactions are discussed. As the first report, we synthesized five histidine-based organocatalyts including histidine as a well-defined and biodegradable natural structure alone and in combination with 2,4,6-trichloro-1,3,5-triazine, benzene-1,3-diamine, dimethyl malonate and dimeric structure applied in the asymmetric intermolecular Heck reaction of aryl halides; their efficiency was compared to each other’s. These phosphine-free palladium catalysts were found as efficient catalytic system which provided the superior efficiency with excellent yields, regioselectivity and enantioselectivity. In these among, histidine with 2,4,6-trichloro-1,3,5-triazine which generate the star like molecule palladium catalyst gave the best activity in asymmetric intermolecular Heck reaction with excellent yields and good regio- and enantioselectivity under mild reaction conditions. The asymmetric intermolecular Heck reaction has been limited to aryl and vinyl triflates or aryl iodide in the rare reports of available Pd catalysts. Herein, we extend the reaction to aryl bromides. In addition, the scope of reaction was examined in two different techniques: conventional heating and microwave irradiation and compared. For the first time, microwave irradiation sintering is successfully used for this reaction. Comparison of catalytic activities of our catalyst (Pd/His) with literature examples confirmed our success.},
     year = {2020}
    }
    

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  • TY  - JOUR
    T1  - Asymmetric Intermolecular Heck Reaction of Aryl Halides by Pd-histidine Organocatalysts
    AU  - Abdol Reza Hajipour
    AU  - Zahra Khorsandi
    Y1  - 2020/06/28
    PY  - 2020
    N1  - https://doi.org/10.11648/j.mc.20200802.11
    DO  - 10.11648/j.mc.20200802.11
    T2  - Modern Chemistry
    JF  - Modern Chemistry
    JO  - Modern Chemistry
    SP  - 18
    EP  - 22
    PB  - Science Publishing Group
    SN  - 2329-180X
    UR  - https://doi.org/10.11648/j.mc.20200802.11
    AB  - Extensive studies of asymmetric intermolecular Heck reaction are described and provide a deeper insight into histidine-catalyzed. In particular, aspects of enantio- as well as diastereoselectivity of these reactions are discussed. As the first report, we synthesized five histidine-based organocatalyts including histidine as a well-defined and biodegradable natural structure alone and in combination with 2,4,6-trichloro-1,3,5-triazine, benzene-1,3-diamine, dimethyl malonate and dimeric structure applied in the asymmetric intermolecular Heck reaction of aryl halides; their efficiency was compared to each other’s. These phosphine-free palladium catalysts were found as efficient catalytic system which provided the superior efficiency with excellent yields, regioselectivity and enantioselectivity. In these among, histidine with 2,4,6-trichloro-1,3,5-triazine which generate the star like molecule palladium catalyst gave the best activity in asymmetric intermolecular Heck reaction with excellent yields and good regio- and enantioselectivity under mild reaction conditions. The asymmetric intermolecular Heck reaction has been limited to aryl and vinyl triflates or aryl iodide in the rare reports of available Pd catalysts. Herein, we extend the reaction to aryl bromides. In addition, the scope of reaction was examined in two different techniques: conventional heating and microwave irradiation and compared. For the first time, microwave irradiation sintering is successfully used for this reaction. Comparison of catalytic activities of our catalyst (Pd/His) with literature examples confirmed our success.
    VL  - 8
    IS  - 2
    ER  - 

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Author Information
  • Department of Chemistry, Isfahan University of Technology, Isfahan, Iran

  • Department of Chemistry, Isfahan University of Technology, Isfahan, Iran

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