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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:
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
Descripción
Sumario: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.