Ligand-Enabled γ-C(sp3)?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 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.
Ghiringhelli, Francesca,Ghosh, Kiron Kumar,Mondal, Arup,Uttry, Alexander,Wedi, Philipp,van Gemmeren, Manuel
supporting information
p. 12848 - 12852
(2020/06/25)
Ligand-Enabled PdII-Catalyzed Iterative γ-C(sp3)?H Arylation of Free Aliphatic Acid
C?H functionalization of aliphatic carboxylic acids without attaching exogenous auxiliary has been so far limited at the proximal β-position. In this work, we demonstrate a ligand enabled palladium catalyzed first regioselective distal γ-C(sp3)?H function