A Predictably Selective Palladium-Catalyzed Aliphatic C–H Oxygenation
Dmitry P. Lubov, М. В. Шашков, Andrey A. Nefedov, Konstantin P. Bryliakov
Abstract
)-H groups with peroxycarboxylic acids in the presence of palladium tris(pyridylmethyl)amine complex (0.6 mol %) is reported, providing the corresponding hydroxylated derivatives in up to 94% yields. The oxidation of 3° C-H groups occurs stereospecifically, with the catalyst system demonstrating extremely high sensitivity to electronic effects (adamantane oxidation: 3°:2° up to >300). This suggests potential applications for the 3°-regioselective oxidative functionalization of complex molecules of natural origin.
Topics & Concepts
ChemistryPalladiumRegioselectivityCatalysisAmine gas treatingAdamantaneMoleculeReactivity (psychology)OxygenationOxidative phosphorylationSurface modificationCombinatorial chemistryMedicinal chemistryOrganic chemistryPhysical chemistryPathologyMedicineEcologyAlternative medicineBiologyBiochemistryCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsMetal-Catalyzed Oxygenation Mechanisms