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Rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner
The directed oxidative C–H/C–H cross-coupling reactions between a functionalized arene and a heteroarene typically exhibit an electronic bias for the heteroaromatic coupling partner. Disclosed herein is a conception of directing group enabled-switching of the electronic bias for coupling partner fro...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6114993/ https://www.ncbi.nlm.nih.gov/pubmed/30310621 http://dx.doi.org/10.1039/c8sc02529k |
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author | Wu, Yimin Li, Wei Jiang, Linfeng Zhang, Luoqiang Lan, Jingbo You, Jingsong |
author_facet | Wu, Yimin Li, Wei Jiang, Linfeng Zhang, Luoqiang Lan, Jingbo You, Jingsong |
author_sort | Wu, Yimin |
collection | PubMed |
description | The directed oxidative C–H/C–H cross-coupling reactions between a functionalized arene and a heteroarene typically exhibit an electronic bias for the heteroaromatic coupling partner. Disclosed herein is a conception of directing group enabled-switching of the electronic bias for coupling partner from the electron-deficient to electron-rich heteroarene, demonstrating that the modification of the directing group may match the latent reactivity of heteroarene substrates caused by the distinctly different electronic nature. In this work, we develop a Rh(iii)-catalyzed ortho-heteroarylation of phenols with greatly important electron-rich heteroarenes such as benzothiophene, benzofuran, thiophene, furan and pyrrole via two-fold C–H activation, which presents broad substrate scopes of both phenols and electron-rich heteroarenes and shows the advantage of tolerance of reactive functional groups, especially halogen. This work also provides a new strategy for the construction of π-conjugated furan-fused heteroacenes prevalent in materials science in dramatically simplified procedures, which makes the protocol highly applicable. |
format | Online Article Text |
id | pubmed-6114993 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-61149932018-10-11 Rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner Wu, Yimin Li, Wei Jiang, Linfeng Zhang, Luoqiang Lan, Jingbo You, Jingsong Chem Sci Chemistry The directed oxidative C–H/C–H cross-coupling reactions between a functionalized arene and a heteroarene typically exhibit an electronic bias for the heteroaromatic coupling partner. Disclosed herein is a conception of directing group enabled-switching of the electronic bias for coupling partner from the electron-deficient to electron-rich heteroarene, demonstrating that the modification of the directing group may match the latent reactivity of heteroarene substrates caused by the distinctly different electronic nature. In this work, we develop a Rh(iii)-catalyzed ortho-heteroarylation of phenols with greatly important electron-rich heteroarenes such as benzothiophene, benzofuran, thiophene, furan and pyrrole via two-fold C–H activation, which presents broad substrate scopes of both phenols and electron-rich heteroarenes and shows the advantage of tolerance of reactive functional groups, especially halogen. This work also provides a new strategy for the construction of π-conjugated furan-fused heteroacenes prevalent in materials science in dramatically simplified procedures, which makes the protocol highly applicable. Royal Society of Chemistry 2018-07-18 /pmc/articles/PMC6114993/ /pubmed/30310621 http://dx.doi.org/10.1039/c8sc02529k Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
spellingShingle | Chemistry Wu, Yimin Li, Wei Jiang, Linfeng Zhang, Luoqiang Lan, Jingbo You, Jingsong Rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner |
title | Rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner
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title_full | Rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner
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title_fullStr | Rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner
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title_full_unstemmed | Rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner
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title_short | Rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner
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title_sort | rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6114993/ https://www.ncbi.nlm.nih.gov/pubmed/30310621 http://dx.doi.org/10.1039/c8sc02529k |
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