Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids

A flexible two-step, one-pot procedure was developed to synthesize 2-aryl propionic acids including the anti-inflammatory drugs naproxen and flurbiprofen. Optimal results were obtained in the presence of the novel ligand neoisopinocampheyldiphenylphosphine (NISPCPP) (9) which enabled the efficient s...

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Detalles Bibliográficos
Autores principales: Neumann, Helfried, Sergeev, Alexey G., Spannenberg, Anke, Beller, Matthias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7435766/
https://www.ncbi.nlm.nih.gov/pubmed/32731527
http://dx.doi.org/10.3390/molecules25153421
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author Neumann, Helfried
Sergeev, Alexey G.
Spannenberg, Anke
Beller, Matthias
author_facet Neumann, Helfried
Sergeev, Alexey G.
Spannenberg, Anke
Beller, Matthias
author_sort Neumann, Helfried
collection PubMed
description A flexible two-step, one-pot procedure was developed to synthesize 2-aryl propionic acids including the anti-inflammatory drugs naproxen and flurbiprofen. Optimal results were obtained in the presence of the novel ligand neoisopinocampheyldiphenylphosphine (NISPCPP) (9) which enabled the efficient sequential palladium-catalyzed Heck coupling of aryl bromides with ethylene and hydroxycarbonylation of the resulting styrenes to 2-aryl propionic acids. This cascade transformation leads with high regioselectivity to the desired products in good yields and avoids the need for additional purification steps.
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spelling pubmed-74357662020-08-25 Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids Neumann, Helfried Sergeev, Alexey G. Spannenberg, Anke Beller, Matthias Molecules Communication A flexible two-step, one-pot procedure was developed to synthesize 2-aryl propionic acids including the anti-inflammatory drugs naproxen and flurbiprofen. Optimal results were obtained in the presence of the novel ligand neoisopinocampheyldiphenylphosphine (NISPCPP) (9) which enabled the efficient sequential palladium-catalyzed Heck coupling of aryl bromides with ethylene and hydroxycarbonylation of the resulting styrenes to 2-aryl propionic acids. This cascade transformation leads with high regioselectivity to the desired products in good yields and avoids the need for additional purification steps. MDPI 2020-07-28 /pmc/articles/PMC7435766/ /pubmed/32731527 http://dx.doi.org/10.3390/molecules25153421 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Neumann, Helfried
Sergeev, Alexey G.
Spannenberg, Anke
Beller, Matthias
Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids
title Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids
title_full Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids
title_fullStr Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids
title_full_unstemmed Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids
title_short Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids
title_sort efficient palladium-catalyzed synthesis of 2-aryl propionic acids
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7435766/
https://www.ncbi.nlm.nih.gov/pubmed/32731527
http://dx.doi.org/10.3390/molecules25153421
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