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Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry

Transition-metal catalyzed asymmetric cyclization of 1,6-enynes has emerged as a powerful method for the construction of carbocycles and heterocycles. However, very rare examples worked under electrochemical conditions. We report herein a Co-catalyzed enantioselective intramolecular reductive coupli...

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Autores principales: Gao, Shiquan, Wang, Chen, Yang, Junfeng, Zhang, Junliang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9998880/
https://www.ncbi.nlm.nih.gov/pubmed/36894526
http://dx.doi.org/10.1038/s41467-023-36704-9
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author Gao, Shiquan
Wang, Chen
Yang, Junfeng
Zhang, Junliang
author_facet Gao, Shiquan
Wang, Chen
Yang, Junfeng
Zhang, Junliang
author_sort Gao, Shiquan
collection PubMed
description Transition-metal catalyzed asymmetric cyclization of 1,6-enynes has emerged as a powerful method for the construction of carbocycles and heterocycles. However, very rare examples worked under electrochemical conditions. We report herein a Co-catalyzed enantioselective intramolecular reductive coupling of enynes via electrochemistry using H(2)O as hydride source. The products were obtained in good yields with high regio- and enantioselectivities. It represents the rare progress on the cobalt-catalyzed enantioselective transformation via electrochemistry with a general substrate scope. DFT studies explored the possible reaction pathways and revealed that the oxidative cyclization of enynes by LCo(I) is more favorable than oxidative addition of H(2)O or other pathways.
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spelling pubmed-99988802023-03-11 Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry Gao, Shiquan Wang, Chen Yang, Junfeng Zhang, Junliang Nat Commun Article Transition-metal catalyzed asymmetric cyclization of 1,6-enynes has emerged as a powerful method for the construction of carbocycles and heterocycles. However, very rare examples worked under electrochemical conditions. We report herein a Co-catalyzed enantioselective intramolecular reductive coupling of enynes via electrochemistry using H(2)O as hydride source. The products were obtained in good yields with high regio- and enantioselectivities. It represents the rare progress on the cobalt-catalyzed enantioselective transformation via electrochemistry with a general substrate scope. DFT studies explored the possible reaction pathways and revealed that the oxidative cyclization of enynes by LCo(I) is more favorable than oxidative addition of H(2)O or other pathways. Nature Publishing Group UK 2023-03-09 /pmc/articles/PMC9998880/ /pubmed/36894526 http://dx.doi.org/10.1038/s41467-023-36704-9 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
Gao, Shiquan
Wang, Chen
Yang, Junfeng
Zhang, Junliang
Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry
title Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry
title_full Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry
title_fullStr Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry
title_full_unstemmed Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry
title_short Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry
title_sort cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9998880/
https://www.ncbi.nlm.nih.gov/pubmed/36894526
http://dx.doi.org/10.1038/s41467-023-36704-9
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AT wangchen cobaltcatalyzedenantioselectiveintramolecularreductivecyclizationviaelectrochemistry
AT yangjunfeng cobaltcatalyzedenantioselectiveintramolecularreductivecyclizationviaelectrochemistry
AT zhangjunliang cobaltcatalyzedenantioselectiveintramolecularreductivecyclizationviaelectrochemistry