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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...

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Autores principales: Wu, Yimin, Li, Wei, Jiang, Linfeng, Zhang, Luoqiang, Lan, Jingbo, You, Jingsong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
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.
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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
title_full Rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner
title_fullStr Rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner
title_full_unstemmed Rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner
title_short Rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner
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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