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Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes
Described here is a modular strategy for the rapid synthesis of β-functionalized electron-rich naphthalenes, a family of valuable molecules lacking general access previously. Our approach employs an intermolecular benzannulation of in situ generated isobenzopyrylium ions with various electron-rich a...
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/PMC8163147/ https://www.ncbi.nlm.nih.gov/pubmed/34094164 http://dx.doi.org/10.1039/d0sc02502j |
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author | Wu, An Qian, Hui Zhao, Wanxiang Sun, Jianwei |
author_facet | Wu, An Qian, Hui Zhao, Wanxiang Sun, Jianwei |
author_sort | Wu, An |
collection | PubMed |
description | Described here is a modular strategy for the rapid synthesis of β-functionalized electron-rich naphthalenes, a family of valuable molecules lacking general access previously. Our approach employs an intermolecular benzannulation of in situ generated isobenzopyrylium ions with various electron-rich alkynes, which were not well utilized for this type of reaction before. These reactions not only feature a broad scope, complete regioselectivity, and mild conditions, but also exhibit unusual product divergence depending on the substrate substitution pattern. This divergence allows further expansion of the product diversity. Control experiments provided preliminary insights into the reaction mechanism. |
format | Online Article Text |
id | pubmed-8163147 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81631472021-06-04 Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes Wu, An Qian, Hui Zhao, Wanxiang Sun, Jianwei Chem Sci Chemistry Described here is a modular strategy for the rapid synthesis of β-functionalized electron-rich naphthalenes, a family of valuable molecules lacking general access previously. Our approach employs an intermolecular benzannulation of in situ generated isobenzopyrylium ions with various electron-rich alkynes, which were not well utilized for this type of reaction before. These reactions not only feature a broad scope, complete regioselectivity, and mild conditions, but also exhibit unusual product divergence depending on the substrate substitution pattern. This divergence allows further expansion of the product diversity. Control experiments provided preliminary insights into the reaction mechanism. The Royal Society of Chemistry 2020-07-06 /pmc/articles/PMC8163147/ /pubmed/34094164 http://dx.doi.org/10.1039/d0sc02502j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Wu, An Qian, Hui Zhao, Wanxiang Sun, Jianwei Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes |
title | Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes |
title_full | Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes |
title_fullStr | Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes |
title_full_unstemmed | Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes |
title_short | Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes |
title_sort | benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8163147/ https://www.ncbi.nlm.nih.gov/pubmed/34094164 http://dx.doi.org/10.1039/d0sc02502j |
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