Ligand‐Enabled γ‐C(sp(3))−H Olefination of Free Carboxylic Acids

We report the ligand‐enabled C−H activation/olefination of free carboxylic acids in the γ‐position. Through an intramolecular Michael addition, δ‐lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium‐catalyzed activation of free carboxyli...

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Detalles Bibliográficos
Autores principales: Ghosh, Kiron Kumar, Uttry, Alexander, Mondal, Arup, Ghiringhelli, Francesca, Wedi, Philipp, van Gemmeren, Manuel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7496353/
https://www.ncbi.nlm.nih.gov/pubmed/32250014
http://dx.doi.org/10.1002/anie.202002362
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author Ghosh, Kiron Kumar
Uttry, Alexander
Mondal, Arup
Ghiringhelli, Francesca
Wedi, Philipp
van Gemmeren, Manuel
author_facet Ghosh, Kiron Kumar
Uttry, Alexander
Mondal, Arup
Ghiringhelli, Francesca
Wedi, Philipp
van Gemmeren, Manuel
author_sort Ghosh, Kiron Kumar
collection PubMed
description We report the ligand‐enabled C−H activation/olefination of free carboxylic acids in the γ‐position. Through an intramolecular Michael addition, δ‐lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium‐catalyzed activation of free carboxylic acids in the γ‐position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.
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spelling pubmed-74963532020-09-25 Ligand‐Enabled γ‐C(sp(3))−H Olefination of Free Carboxylic Acids Ghosh, Kiron Kumar Uttry, Alexander Mondal, Arup Ghiringhelli, Francesca Wedi, Philipp van Gemmeren, Manuel Angew Chem Int Ed Engl Communications We report the ligand‐enabled C−H activation/olefination of free carboxylic acids in the γ‐position. Through an intramolecular Michael addition, δ‐lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium‐catalyzed activation of free carboxylic acids in the γ‐position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported. John Wiley and Sons Inc. 2020-05-18 2020-07-27 /pmc/articles/PMC7496353/ /pubmed/32250014 http://dx.doi.org/10.1002/anie.202002362 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Ghosh, Kiron Kumar
Uttry, Alexander
Mondal, Arup
Ghiringhelli, Francesca
Wedi, Philipp
van Gemmeren, Manuel
Ligand‐Enabled γ‐C(sp(3))−H Olefination of Free Carboxylic Acids
title Ligand‐Enabled γ‐C(sp(3))−H Olefination of Free Carboxylic Acids
title_full Ligand‐Enabled γ‐C(sp(3))−H Olefination of Free Carboxylic Acids
title_fullStr Ligand‐Enabled γ‐C(sp(3))−H Olefination of Free Carboxylic Acids
title_full_unstemmed Ligand‐Enabled γ‐C(sp(3))−H Olefination of Free Carboxylic Acids
title_short Ligand‐Enabled γ‐C(sp(3))−H Olefination of Free Carboxylic Acids
title_sort ligand‐enabled γ‐c(sp(3))−h olefination of free carboxylic acids
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7496353/
https://www.ncbi.nlm.nih.gov/pubmed/32250014
http://dx.doi.org/10.1002/anie.202002362
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