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Nickel-catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes

Developing efficient strategies to realize divergent arylation of dienes has been a long-standing synthetic challenge. Herein, a nickel catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes has been demonstrated through the regulation of ligands and additives. In the presence of Mn/NEt(3), the Mi...

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Autores principales: Zhang, Wei-Song, Ji, Ding-Wei, Li, Ying, Zhang, Xiang-Xin, Mei, Yong-Kang, Chen, Bing-Zhi, Chen, Qing-An
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9902549/
https://www.ncbi.nlm.nih.gov/pubmed/36746964
http://dx.doi.org/10.1038/s41467-023-36237-1
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author Zhang, Wei-Song
Ji, Ding-Wei
Li, Ying
Zhang, Xiang-Xin
Mei, Yong-Kang
Chen, Bing-Zhi
Chen, Qing-An
author_facet Zhang, Wei-Song
Ji, Ding-Wei
Li, Ying
Zhang, Xiang-Xin
Mei, Yong-Kang
Chen, Bing-Zhi
Chen, Qing-An
author_sort Zhang, Wei-Song
collection PubMed
description Developing efficient strategies to realize divergent arylation of dienes has been a long-standing synthetic challenge. Herein, a nickel catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes has been demonstrated through the regulation of ligands and additives. In the presence of Mn/NEt(3), the Mizoroki–Heck reaction of dienes delivers linear products under Ni(dppe)Cl(2) catalysis in high regio- and stereoselectivities. With the help of catalytic amount of organoboron and NaF, the use of bulky ligand IPr diverts the selectivity from linear products to branched products. Highly aryl-substituted compounds can be transformed from dispersive Mizoroki–Heck products programmatically. Preliminary experimental studies are carried out to elucidate the role of additives.
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spelling pubmed-99025492023-02-08 Nickel-catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes Zhang, Wei-Song Ji, Ding-Wei Li, Ying Zhang, Xiang-Xin Mei, Yong-Kang Chen, Bing-Zhi Chen, Qing-An Nat Commun Article Developing efficient strategies to realize divergent arylation of dienes has been a long-standing synthetic challenge. Herein, a nickel catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes has been demonstrated through the regulation of ligands and additives. In the presence of Mn/NEt(3), the Mizoroki–Heck reaction of dienes delivers linear products under Ni(dppe)Cl(2) catalysis in high regio- and stereoselectivities. With the help of catalytic amount of organoboron and NaF, the use of bulky ligand IPr diverts the selectivity from linear products to branched products. Highly aryl-substituted compounds can be transformed from dispersive Mizoroki–Heck products programmatically. Preliminary experimental studies are carried out to elucidate the role of additives. Nature Publishing Group UK 2023-02-06 /pmc/articles/PMC9902549/ /pubmed/36746964 http://dx.doi.org/10.1038/s41467-023-36237-1 Text en © The Author(s) 2023 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, Wei-Song
Ji, Ding-Wei
Li, Ying
Zhang, Xiang-Xin
Mei, Yong-Kang
Chen, Bing-Zhi
Chen, Qing-An
Nickel-catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes
title Nickel-catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes
title_full Nickel-catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes
title_fullStr Nickel-catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes
title_full_unstemmed Nickel-catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes
title_short Nickel-catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes
title_sort nickel-catalyzed divergent mizoroki–heck reaction of 1,3-dienes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9902549/
https://www.ncbi.nlm.nih.gov/pubmed/36746964
http://dx.doi.org/10.1038/s41467-023-36237-1
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