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Non-C(2)-Symmetric Bis-Benzimidazolium Salt Applied in the Synthesis of Sterically Hindered Biaryls

A novel non-C(2)-symmetric bis-benzimidazolium salt derived from (±)-valinol has been prepared by a simple and straightforward process in good yield. The structure of bis-benzimidazolium salt provided a bulky steric group on the ethylene bridge; which facilitates the catalytic efficacy in the C(sp(2...

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Autores principales: Chen, Yen-Hsin, Huang, Shu-Jyun, Hsu, Tung-Yu, Hung, Pei-Yu, Wei, Ting-Rong, Lee, Dong-Sheng, Lu, Ta-Jung
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8588361/
https://www.ncbi.nlm.nih.gov/pubmed/34771121
http://dx.doi.org/10.3390/molecules26216703
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author Chen, Yen-Hsin
Huang, Shu-Jyun
Hsu, Tung-Yu
Hung, Pei-Yu
Wei, Ting-Rong
Lee, Dong-Sheng
Lu, Ta-Jung
author_facet Chen, Yen-Hsin
Huang, Shu-Jyun
Hsu, Tung-Yu
Hung, Pei-Yu
Wei, Ting-Rong
Lee, Dong-Sheng
Lu, Ta-Jung
author_sort Chen, Yen-Hsin
collection PubMed
description A novel non-C(2)-symmetric bis-benzimidazolium salt derived from (±)-valinol has been prepared by a simple and straightforward process in good yield. The structure of bis-benzimidazolium salt provided a bulky steric group on the ethylene bridge; which facilitates the catalytic efficacy in the C(sp(2))–C(sp(2)) formation. Its catalytic activity in Suzuki–Miyaura cross-coupling reaction of unactivated aryl chlorides has been found to have high efficacy in 1 mol% Pd loading. This protocol demonstrated the potential on the synthesis of sterically hindered biaryls.
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spelling pubmed-85883612021-11-13 Non-C(2)-Symmetric Bis-Benzimidazolium Salt Applied in the Synthesis of Sterically Hindered Biaryls Chen, Yen-Hsin Huang, Shu-Jyun Hsu, Tung-Yu Hung, Pei-Yu Wei, Ting-Rong Lee, Dong-Sheng Lu, Ta-Jung Molecules Article A novel non-C(2)-symmetric bis-benzimidazolium salt derived from (±)-valinol has been prepared by a simple and straightforward process in good yield. The structure of bis-benzimidazolium salt provided a bulky steric group on the ethylene bridge; which facilitates the catalytic efficacy in the C(sp(2))–C(sp(2)) formation. Its catalytic activity in Suzuki–Miyaura cross-coupling reaction of unactivated aryl chlorides has been found to have high efficacy in 1 mol% Pd loading. This protocol demonstrated the potential on the synthesis of sterically hindered biaryls. MDPI 2021-11-05 /pmc/articles/PMC8588361/ /pubmed/34771121 http://dx.doi.org/10.3390/molecules26216703 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Chen, Yen-Hsin
Huang, Shu-Jyun
Hsu, Tung-Yu
Hung, Pei-Yu
Wei, Ting-Rong
Lee, Dong-Sheng
Lu, Ta-Jung
Non-C(2)-Symmetric Bis-Benzimidazolium Salt Applied in the Synthesis of Sterically Hindered Biaryls
title Non-C(2)-Symmetric Bis-Benzimidazolium Salt Applied in the Synthesis of Sterically Hindered Biaryls
title_full Non-C(2)-Symmetric Bis-Benzimidazolium Salt Applied in the Synthesis of Sterically Hindered Biaryls
title_fullStr Non-C(2)-Symmetric Bis-Benzimidazolium Salt Applied in the Synthesis of Sterically Hindered Biaryls
title_full_unstemmed Non-C(2)-Symmetric Bis-Benzimidazolium Salt Applied in the Synthesis of Sterically Hindered Biaryls
title_short Non-C(2)-Symmetric Bis-Benzimidazolium Salt Applied in the Synthesis of Sterically Hindered Biaryls
title_sort non-c(2)-symmetric bis-benzimidazolium salt applied in the synthesis of sterically hindered biaryls
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8588361/
https://www.ncbi.nlm.nih.gov/pubmed/34771121
http://dx.doi.org/10.3390/molecules26216703
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