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meta‐Selective C−H Borylation of Benzylamine‐, Phenethylamine‐, and Phenylpropylamine‐Derived Amides Enabled by a Single Anionic Ligand

Selective functionalization at the meta position of arenes remains a significant challenge. In this work, we demonstrate that a single anionic bipyridine ligand bearing a remote sulfonate group enables selective iridium‐catalyzed borylation of a range of common amine‐containing aromatic molecules at...

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Autores principales: Davis, Holly J., Genov, Georgi R., Phipps, Robert J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5656929/
https://www.ncbi.nlm.nih.gov/pubmed/28877397
http://dx.doi.org/10.1002/anie.201708967
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author Davis, Holly J.
Genov, Georgi R.
Phipps, Robert J.
author_facet Davis, Holly J.
Genov, Georgi R.
Phipps, Robert J.
author_sort Davis, Holly J.
collection PubMed
description Selective functionalization at the meta position of arenes remains a significant challenge. In this work, we demonstrate that a single anionic bipyridine ligand bearing a remote sulfonate group enables selective iridium‐catalyzed borylation of a range of common amine‐containing aromatic molecules at the arene meta position. We propose that this selectivity is the result of a key hydrogen bonding interaction between the substrate and catalyst. The scope of this meta‐selective borylation is demonstrated on amides derived from benzylamines, phenethylamines and phenylpropylamines; amine‐containing building blocks of great utility in many applications.
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spelling pubmed-56569292017-11-01 meta‐Selective C−H Borylation of Benzylamine‐, Phenethylamine‐, and Phenylpropylamine‐Derived Amides Enabled by a Single Anionic Ligand Davis, Holly J. Genov, Georgi R. Phipps, Robert J. Angew Chem Int Ed Engl Communications Selective functionalization at the meta position of arenes remains a significant challenge. In this work, we demonstrate that a single anionic bipyridine ligand bearing a remote sulfonate group enables selective iridium‐catalyzed borylation of a range of common amine‐containing aromatic molecules at the arene meta position. We propose that this selectivity is the result of a key hydrogen bonding interaction between the substrate and catalyst. The scope of this meta‐selective borylation is demonstrated on amides derived from benzylamines, phenethylamines and phenylpropylamines; amine‐containing building blocks of great utility in many applications. John Wiley and Sons Inc. 2017-09-19 2017-10-16 /pmc/articles/PMC5656929/ /pubmed/28877397 http://dx.doi.org/10.1002/anie.201708967 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
Davis, Holly J.
Genov, Georgi R.
Phipps, Robert J.
meta‐Selective C−H Borylation of Benzylamine‐, Phenethylamine‐, and Phenylpropylamine‐Derived Amides Enabled by a Single Anionic Ligand
title meta‐Selective C−H Borylation of Benzylamine‐, Phenethylamine‐, and Phenylpropylamine‐Derived Amides Enabled by a Single Anionic Ligand
title_full meta‐Selective C−H Borylation of Benzylamine‐, Phenethylamine‐, and Phenylpropylamine‐Derived Amides Enabled by a Single Anionic Ligand
title_fullStr meta‐Selective C−H Borylation of Benzylamine‐, Phenethylamine‐, and Phenylpropylamine‐Derived Amides Enabled by a Single Anionic Ligand
title_full_unstemmed meta‐Selective C−H Borylation of Benzylamine‐, Phenethylamine‐, and Phenylpropylamine‐Derived Amides Enabled by a Single Anionic Ligand
title_short meta‐Selective C−H Borylation of Benzylamine‐, Phenethylamine‐, and Phenylpropylamine‐Derived Amides Enabled by a Single Anionic Ligand
title_sort meta‐selective c−h borylation of benzylamine‐, phenethylamine‐, and phenylpropylamine‐derived amides enabled by a single anionic ligand
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5656929/
https://www.ncbi.nlm.nih.gov/pubmed/28877397
http://dx.doi.org/10.1002/anie.201708967
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