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Oxidative [4+2] annulation of styrenes with alkynes under external-oxidant-free conditions
The sequenced Diels–Alder/oxidation reaction represents a powerful route for the construction of aromatic compounds in organic synthesis. The oxidative Diels–Alder reaction with H(2) evolution would be a more ideal approach that can avoid the additional oxidation procedure and stoichiometric oxidant...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5964314/ https://www.ncbi.nlm.nih.gov/pubmed/29581484 http://dx.doi.org/10.1038/s41467-018-03534-z |
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author | Zhang, Guoting Lin, Yulin Luo, Xu Hu, Xia Chen, Cong Lei, Aiwen |
author_facet | Zhang, Guoting Lin, Yulin Luo, Xu Hu, Xia Chen, Cong Lei, Aiwen |
author_sort | Zhang, Guoting |
collection | PubMed |
description | The sequenced Diels–Alder/oxidation reaction represents a powerful route for the construction of aromatic compounds in organic synthesis. The oxidative Diels–Alder reaction with H(2) evolution would be a more ideal approach that can avoid the additional oxidation procedure and stoichiometric oxidant. Herein, an oxidative [4 + 2] annulation reaction of styrene derivatives with electron-rich dienophiles accompanying the H(2) generation has been developed by using the synergistic merger of photoredox and cobaloxime catalyst. With respect to atom and step-economy ideals, this dual catalytic system enables the formation of high-value molecules from feedstock chemicals in a single step under room temperature. |
format | Online Article Text |
id | pubmed-5964314 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-59643142018-05-24 Oxidative [4+2] annulation of styrenes with alkynes under external-oxidant-free conditions Zhang, Guoting Lin, Yulin Luo, Xu Hu, Xia Chen, Cong Lei, Aiwen Nat Commun Article The sequenced Diels–Alder/oxidation reaction represents a powerful route for the construction of aromatic compounds in organic synthesis. The oxidative Diels–Alder reaction with H(2) evolution would be a more ideal approach that can avoid the additional oxidation procedure and stoichiometric oxidant. Herein, an oxidative [4 + 2] annulation reaction of styrene derivatives with electron-rich dienophiles accompanying the H(2) generation has been developed by using the synergistic merger of photoredox and cobaloxime catalyst. With respect to atom and step-economy ideals, this dual catalytic system enables the formation of high-value molecules from feedstock chemicals in a single step under room temperature. Nature Publishing Group UK 2018-03-26 /pmc/articles/PMC5964314/ /pubmed/29581484 http://dx.doi.org/10.1038/s41467-018-03534-z 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 Zhang, Guoting Lin, Yulin Luo, Xu Hu, Xia Chen, Cong Lei, Aiwen Oxidative [4+2] annulation of styrenes with alkynes under external-oxidant-free conditions |
title | Oxidative [4+2] annulation of styrenes with alkynes under external-oxidant-free conditions |
title_full | Oxidative [4+2] annulation of styrenes with alkynes under external-oxidant-free conditions |
title_fullStr | Oxidative [4+2] annulation of styrenes with alkynes under external-oxidant-free conditions |
title_full_unstemmed | Oxidative [4+2] annulation of styrenes with alkynes under external-oxidant-free conditions |
title_short | Oxidative [4+2] annulation of styrenes with alkynes under external-oxidant-free conditions |
title_sort | oxidative [4+2] annulation of styrenes with alkynes under external-oxidant-free conditions |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5964314/ https://www.ncbi.nlm.nih.gov/pubmed/29581484 http://dx.doi.org/10.1038/s41467-018-03534-z |
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