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A Simple and Practical Bis-N-Heterocyclic Carbene as an Efficient Ligand in Cu-Catalyzed Glaser Reaction

Conjugated diyne derivatives are important scaffolds in modern organic synthetic chemistry. Using the Glaser reaction involves the coupling of terminal alkynes which can efficiently produce conjugated diyne derivatives, while the use of a stoichiometric amount of copper salts, strong inorganic base,...

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Detalles Bibliográficos
Autores principales: Liu, Jie, Zhu, Yao, Luo, Jun, Zhu, Ziyi, Zhao, Lin, Zeng, Xiaoyan, Li, Dongdong, Chen, Jun, Lan, Xiaobing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10343847/
https://www.ncbi.nlm.nih.gov/pubmed/37446745
http://dx.doi.org/10.3390/molecules28135083
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author Liu, Jie
Zhu, Yao
Luo, Jun
Zhu, Ziyi
Zhao, Lin
Zeng, Xiaoyan
Li, Dongdong
Chen, Jun
Lan, Xiaobing
author_facet Liu, Jie
Zhu, Yao
Luo, Jun
Zhu, Ziyi
Zhao, Lin
Zeng, Xiaoyan
Li, Dongdong
Chen, Jun
Lan, Xiaobing
author_sort Liu, Jie
collection PubMed
description Conjugated diyne derivatives are important scaffolds in modern organic synthetic chemistry. Using the Glaser reaction involves the coupling of terminal alkynes which can efficiently produce conjugated diyne derivatives, while the use of a stoichiometric amount of copper salts, strong inorganic base, and excess oxidants is generally needed. Developing an environmentally friendly and effective method for the construction of symmetrical 1,3-diynes compounds by Glaser coupling is still highly desirable. In this study, we present an economical method for the production of symmetric diynes starting from various terminal acetylenes in a Glaser reaction. A simple and practical bis-N-heterocyclic carbene ligand has been introduced as efficient ligands for the Cu-catalyzed Glaser reaction. High product yields were obtained at 100 °C for a variety of substrates including aliphatic and aromatic terminal alkynes and differently substituted terminal alkynes including the highly sterically hindered substrate 2-methoxy ethynylbenzene or 2-trifluoromethyl ethynylbenzene and a series of functional groups, such as trifluoromethyl group, ester group, carboxyl group, and nitrile group. The established protocol is carried out in air under base-free condition and is operationally simple. These research work suggest that bis-N-heterocyclic carbene could also an appealing ligand for Glaser reaction and provide a reference for the preparation of symmetric 1,3-diynes in industrial filed.
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spelling pubmed-103438472023-07-14 A Simple and Practical Bis-N-Heterocyclic Carbene as an Efficient Ligand in Cu-Catalyzed Glaser Reaction Liu, Jie Zhu, Yao Luo, Jun Zhu, Ziyi Zhao, Lin Zeng, Xiaoyan Li, Dongdong Chen, Jun Lan, Xiaobing Molecules Communication Conjugated diyne derivatives are important scaffolds in modern organic synthetic chemistry. Using the Glaser reaction involves the coupling of terminal alkynes which can efficiently produce conjugated diyne derivatives, while the use of a stoichiometric amount of copper salts, strong inorganic base, and excess oxidants is generally needed. Developing an environmentally friendly and effective method for the construction of symmetrical 1,3-diynes compounds by Glaser coupling is still highly desirable. In this study, we present an economical method for the production of symmetric diynes starting from various terminal acetylenes in a Glaser reaction. A simple and practical bis-N-heterocyclic carbene ligand has been introduced as efficient ligands for the Cu-catalyzed Glaser reaction. High product yields were obtained at 100 °C for a variety of substrates including aliphatic and aromatic terminal alkynes and differently substituted terminal alkynes including the highly sterically hindered substrate 2-methoxy ethynylbenzene or 2-trifluoromethyl ethynylbenzene and a series of functional groups, such as trifluoromethyl group, ester group, carboxyl group, and nitrile group. The established protocol is carried out in air under base-free condition and is operationally simple. These research work suggest that bis-N-heterocyclic carbene could also an appealing ligand for Glaser reaction and provide a reference for the preparation of symmetric 1,3-diynes in industrial filed. MDPI 2023-06-29 /pmc/articles/PMC10343847/ /pubmed/37446745 http://dx.doi.org/10.3390/molecules28135083 Text en © 2023 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 Communication
Liu, Jie
Zhu, Yao
Luo, Jun
Zhu, Ziyi
Zhao, Lin
Zeng, Xiaoyan
Li, Dongdong
Chen, Jun
Lan, Xiaobing
A Simple and Practical Bis-N-Heterocyclic Carbene as an Efficient Ligand in Cu-Catalyzed Glaser Reaction
title A Simple and Practical Bis-N-Heterocyclic Carbene as an Efficient Ligand in Cu-Catalyzed Glaser Reaction
title_full A Simple and Practical Bis-N-Heterocyclic Carbene as an Efficient Ligand in Cu-Catalyzed Glaser Reaction
title_fullStr A Simple and Practical Bis-N-Heterocyclic Carbene as an Efficient Ligand in Cu-Catalyzed Glaser Reaction
title_full_unstemmed A Simple and Practical Bis-N-Heterocyclic Carbene as an Efficient Ligand in Cu-Catalyzed Glaser Reaction
title_short A Simple and Practical Bis-N-Heterocyclic Carbene as an Efficient Ligand in Cu-Catalyzed Glaser Reaction
title_sort simple and practical bis-n-heterocyclic carbene as an efficient ligand in cu-catalyzed glaser reaction
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10343847/
https://www.ncbi.nlm.nih.gov/pubmed/37446745
http://dx.doi.org/10.3390/molecules28135083
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