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Cobalt-catalyzed electrooxidative C-H/N-H [4+2] annulation with ethylene or ethyne

Ethylene and ethyne are among the simplest two-carbon building blocks. However, quite limited methods can be applied to incorporate ethylene or ethyne into fine chemicals. Here we demonstrate a cobalt-catalyzed dehydrogenative C–H/N–H [4+2] annulation of aryl/vinyl amides with ethylene or ethyne by...

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Autores principales: Tang, Shan, Wang, Dan, Liu, Yichang, Zeng, Li, Lei, Aiwen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5824839/
https://www.ncbi.nlm.nih.gov/pubmed/29476057
http://dx.doi.org/10.1038/s41467-018-03246-4
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author Tang, Shan
Wang, Dan
Liu, Yichang
Zeng, Li
Lei, Aiwen
author_facet Tang, Shan
Wang, Dan
Liu, Yichang
Zeng, Li
Lei, Aiwen
author_sort Tang, Shan
collection PubMed
description Ethylene and ethyne are among the simplest two-carbon building blocks. However, quite limited methods can be applied to incorporate ethylene or ethyne into fine chemicals. Here we demonstrate a cobalt-catalyzed dehydrogenative C–H/N–H [4+2] annulation of aryl/vinyl amides with ethylene or ethyne by using an electrochemical reaction protocol. Significantly, this work shows an example of electrochemical recycling of cobalt catalyst in oxidative C–H functionalization reactions, avoiding the use of external chemical oxidants and co-oxidants. The electrochemical method provides a reliable and safe way for incorporating gas-phase ethylene or ethyne into fine chemicals. High reaction efficiency and good functional group tolerance are observed under divided electrolytic conditions.
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spelling pubmed-58248392018-02-26 Cobalt-catalyzed electrooxidative C-H/N-H [4+2] annulation with ethylene or ethyne Tang, Shan Wang, Dan Liu, Yichang Zeng, Li Lei, Aiwen Nat Commun Article Ethylene and ethyne are among the simplest two-carbon building blocks. However, quite limited methods can be applied to incorporate ethylene or ethyne into fine chemicals. Here we demonstrate a cobalt-catalyzed dehydrogenative C–H/N–H [4+2] annulation of aryl/vinyl amides with ethylene or ethyne by using an electrochemical reaction protocol. Significantly, this work shows an example of electrochemical recycling of cobalt catalyst in oxidative C–H functionalization reactions, avoiding the use of external chemical oxidants and co-oxidants. The electrochemical method provides a reliable and safe way for incorporating gas-phase ethylene or ethyne into fine chemicals. High reaction efficiency and good functional group tolerance are observed under divided electrolytic conditions. Nature Publishing Group UK 2018-02-23 /pmc/articles/PMC5824839/ /pubmed/29476057 http://dx.doi.org/10.1038/s41467-018-03246-4 Text en © The Author(s) 2018 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/.
spellingShingle Article
Tang, Shan
Wang, Dan
Liu, Yichang
Zeng, Li
Lei, Aiwen
Cobalt-catalyzed electrooxidative C-H/N-H [4+2] annulation with ethylene or ethyne
title Cobalt-catalyzed electrooxidative C-H/N-H [4+2] annulation with ethylene or ethyne
title_full Cobalt-catalyzed electrooxidative C-H/N-H [4+2] annulation with ethylene or ethyne
title_fullStr Cobalt-catalyzed electrooxidative C-H/N-H [4+2] annulation with ethylene or ethyne
title_full_unstemmed Cobalt-catalyzed electrooxidative C-H/N-H [4+2] annulation with ethylene or ethyne
title_short Cobalt-catalyzed electrooxidative C-H/N-H [4+2] annulation with ethylene or ethyne
title_sort cobalt-catalyzed electrooxidative c-h/n-h [4+2] annulation with ethylene or ethyne
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5824839/
https://www.ncbi.nlm.nih.gov/pubmed/29476057
http://dx.doi.org/10.1038/s41467-018-03246-4
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