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Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes
An electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes for the synthesis of C3-functionalized 2-aryl-2,3-dihydrobenzofuran derivatives was achieved. The ring construction starts by a unique α-addition of carbon radicals derived from anodic oxidation of phenols to electron-d...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8152790/ https://www.ncbi.nlm.nih.gov/pubmed/34122860 http://dx.doi.org/10.1039/d0sc01078b |
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author | Zhao, Qiang Jin, Ji-Kang Wang, Jie Zhang, Feng-Lian Wang, Yi-Feng |
author_facet | Zhao, Qiang Jin, Ji-Kang Wang, Jie Zhang, Feng-Lian Wang, Yi-Feng |
author_sort | Zhao, Qiang |
collection | PubMed |
description | An electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes for the synthesis of C3-functionalized 2-aryl-2,3-dihydrobenzofuran derivatives was achieved. The ring construction starts by a unique α-addition of carbon radicals derived from anodic oxidation of phenols to electron-deficient alkenes. The subsequent anodic oxidation of the resulting alkyl radical intermediates followed by trapping with the phenolic hydroxy group assembles the 2,3-dihydrobenzofuran core. Such a pathway enables the installation of various electrophilic functionalities including alkoxycarbonyl, alkylaminocarbonyl, trifluoromethyl, and cyano groups at the C-3 of the 2,3-dihydrobenzofuran framework, which is unattainable by other intermolecular reactions. The application of this method for a rapid synthesis of a bioactive natural product is demonstrated. |
format | Online Article Text |
id | pubmed-8152790 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81527902021-06-11 Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes Zhao, Qiang Jin, Ji-Kang Wang, Jie Zhang, Feng-Lian Wang, Yi-Feng Chem Sci Chemistry An electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes for the synthesis of C3-functionalized 2-aryl-2,3-dihydrobenzofuran derivatives was achieved. The ring construction starts by a unique α-addition of carbon radicals derived from anodic oxidation of phenols to electron-deficient alkenes. The subsequent anodic oxidation of the resulting alkyl radical intermediates followed by trapping with the phenolic hydroxy group assembles the 2,3-dihydrobenzofuran core. Such a pathway enables the installation of various electrophilic functionalities including alkoxycarbonyl, alkylaminocarbonyl, trifluoromethyl, and cyano groups at the C-3 of the 2,3-dihydrobenzofuran framework, which is unattainable by other intermolecular reactions. The application of this method for a rapid synthesis of a bioactive natural product is demonstrated. The Royal Society of Chemistry 2020-03-23 /pmc/articles/PMC8152790/ /pubmed/34122860 http://dx.doi.org/10.1039/d0sc01078b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Zhao, Qiang Jin, Ji-Kang Wang, Jie Zhang, Feng-Lian Wang, Yi-Feng Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes |
title | Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes |
title_full | Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes |
title_fullStr | Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes |
title_full_unstemmed | Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes |
title_short | Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes |
title_sort | radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8152790/ https://www.ncbi.nlm.nih.gov/pubmed/34122860 http://dx.doi.org/10.1039/d0sc01078b |
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