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Ligand‐Enabled γ‐C(sp 3 )−H Olefination of Free Carboxylic Acids
Author(s) -
Ghosh Kiron Kumar,
Uttry Alexander,
Mondal Arup,
Ghiringhelli Francesca,
Wedi Philipp,
Gemmeren Manuel
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202002362
Subject(s) - ligand (biochemistry) , carboxylic acid , chemistry , stereochemistry , organic chemistry , biochemistry , receptor
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.