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

Abdol Reza Hajipour; Zahra Khorsandi

doi:doi:10.11648/j.mc.20200802.11

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

Abdol Reza Hajipour, Zahra Khorsandi

Published in Modern Chemistry (Volume 8, Issue 2)

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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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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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

Abdol Reza Hajipour

Department of Chemistry, Isfahan University of Technology, Isfahan, Iran
Zahra Khorsandi

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

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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}
}

Copy | Download

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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