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Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN(2) pincer ligand

Alkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Here, we show a nickel-catalyzed deaminative Sonogashira coupling of alkylpy...

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Autores principales: Zhang, Xingjie, Qi, Di, Jiao, Chenchen, Liu, Xiaopan, Zhang, Guisheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8361081/
https://www.ncbi.nlm.nih.gov/pubmed/34385455
http://dx.doi.org/10.1038/s41467-021-25222-1
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author Zhang, Xingjie
Qi, Di
Jiao, Chenchen
Liu, Xiaopan
Zhang, Guisheng
author_facet Zhang, Xingjie
Qi, Di
Jiao, Chenchen
Liu, Xiaopan
Zhang, Guisheng
author_sort Zhang, Xingjie
collection PubMed
description Alkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Here, we show a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts. Key to the success of this coupling is the development of an easily accessible and bench-stable amide-type pincer ligand. This ligand allows naturally abundant alkyl amines as alkylating agents in Sonogashira reactions, and produces diverse alkynes in excellent yields under mild conditions. Salient merits of this chemistry include broad substrate scope and functional group tolerance, gram-scale synthesis, one-pot transformation, versatile late-stage derivatizations as well as the use of inexpensive pre-catalyst and readily available substrates. The high efficiency and strong practicability bode well for the widespread applications of this strategy in constructing functional molecules, materials, and fine chemicals.
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spelling pubmed-83610812021-08-19 Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN(2) pincer ligand Zhang, Xingjie Qi, Di Jiao, Chenchen Liu, Xiaopan Zhang, Guisheng Nat Commun Article Alkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Here, we show a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts. Key to the success of this coupling is the development of an easily accessible and bench-stable amide-type pincer ligand. This ligand allows naturally abundant alkyl amines as alkylating agents in Sonogashira reactions, and produces diverse alkynes in excellent yields under mild conditions. Salient merits of this chemistry include broad substrate scope and functional group tolerance, gram-scale synthesis, one-pot transformation, versatile late-stage derivatizations as well as the use of inexpensive pre-catalyst and readily available substrates. The high efficiency and strong practicability bode well for the widespread applications of this strategy in constructing functional molecules, materials, and fine chemicals. Nature Publishing Group UK 2021-08-12 /pmc/articles/PMC8361081/ /pubmed/34385455 http://dx.doi.org/10.1038/s41467-021-25222-1 Text en © The Author(s) 2021 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Zhang, Xingjie
Qi, Di
Jiao, Chenchen
Liu, Xiaopan
Zhang, Guisheng
Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN(2) pincer ligand
title Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN(2) pincer ligand
title_full Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN(2) pincer ligand
title_fullStr Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN(2) pincer ligand
title_full_unstemmed Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN(2) pincer ligand
title_short Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN(2) pincer ligand
title_sort nickel-catalyzed deaminative sonogashira coupling of alkylpyridinium salts enabled by nn(2) pincer ligand
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8361081/
https://www.ncbi.nlm.nih.gov/pubmed/34385455
http://dx.doi.org/10.1038/s41467-021-25222-1
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