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Ruthenium‐Catalyzed C−H Arylation of Benzoic Acids and Indole Carboxylic Acids with Aryl Halides

Herein we report the first Ru‐catalyzed C−H arylation of benzoic acids with readily available aryl (pseudo)halides. The reaction, which does not require the use of silver salt additives, allows the arylation of previously challenging hindered benzoic acids and the use of generally unreactive ortho‐s...

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Autores principales: Simonetti, Marco, Cannas, Diego M., Panigrahi, Adyasha, Kujawa, Szymon, Kryjewski, Michal, Xie, Pan, Larrosa, Igor
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5412846/
https://www.ncbi.nlm.nih.gov/pubmed/27798824
http://dx.doi.org/10.1002/chem.201605068
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author Simonetti, Marco
Cannas, Diego M.
Panigrahi, Adyasha
Kujawa, Szymon
Kryjewski, Michal
Xie, Pan
Larrosa, Igor
author_facet Simonetti, Marco
Cannas, Diego M.
Panigrahi, Adyasha
Kujawa, Szymon
Kryjewski, Michal
Xie, Pan
Larrosa, Igor
author_sort Simonetti, Marco
collection PubMed
description Herein we report the first Ru‐catalyzed C−H arylation of benzoic acids with readily available aryl (pseudo)halides. The reaction, which does not require the use of silver salt additives, allows the arylation of previously challenging hindered benzoic acids and the use of generally unreactive ortho‐substituted halorarenes. Furthermore, our new protocol can efficiently be applied to indole carboxylic acids, thus allowing access to C7‐, C6‐, C5‐ and C4‐arylated indole compounds, a departure from the classical enhanced reactivity of the C2 and C3 positions of indole.
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spelling pubmed-54128462017-05-15 Ruthenium‐Catalyzed C−H Arylation of Benzoic Acids and Indole Carboxylic Acids with Aryl Halides Simonetti, Marco Cannas, Diego M. Panigrahi, Adyasha Kujawa, Szymon Kryjewski, Michal Xie, Pan Larrosa, Igor Chemistry Communications Herein we report the first Ru‐catalyzed C−H arylation of benzoic acids with readily available aryl (pseudo)halides. The reaction, which does not require the use of silver salt additives, allows the arylation of previously challenging hindered benzoic acids and the use of generally unreactive ortho‐substituted halorarenes. Furthermore, our new protocol can efficiently be applied to indole carboxylic acids, thus allowing access to C7‐, C6‐, C5‐ and C4‐arylated indole compounds, a departure from the classical enhanced reactivity of the C2 and C3 positions of indole. John Wiley and Sons Inc. 2016-12-05 2017-01-12 /pmc/articles/PMC5412846/ /pubmed/27798824 http://dx.doi.org/10.1002/chem.201605068 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Simonetti, Marco
Cannas, Diego M.
Panigrahi, Adyasha
Kujawa, Szymon
Kryjewski, Michal
Xie, Pan
Larrosa, Igor
Ruthenium‐Catalyzed C−H Arylation of Benzoic Acids and Indole Carboxylic Acids with Aryl Halides
title Ruthenium‐Catalyzed C−H Arylation of Benzoic Acids and Indole Carboxylic Acids with Aryl Halides
title_full Ruthenium‐Catalyzed C−H Arylation of Benzoic Acids and Indole Carboxylic Acids with Aryl Halides
title_fullStr Ruthenium‐Catalyzed C−H Arylation of Benzoic Acids and Indole Carboxylic Acids with Aryl Halides
title_full_unstemmed Ruthenium‐Catalyzed C−H Arylation of Benzoic Acids and Indole Carboxylic Acids with Aryl Halides
title_short Ruthenium‐Catalyzed C−H Arylation of Benzoic Acids and Indole Carboxylic Acids with Aryl Halides
title_sort ruthenium‐catalyzed c−h arylation of benzoic acids and indole carboxylic acids with aryl halides
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5412846/
https://www.ncbi.nlm.nih.gov/pubmed/27798824
http://dx.doi.org/10.1002/chem.201605068
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