Ligand-promoted palladium-catalyzed β-methylene C–H arylation of primary aldehydes
Ke Yang, Zhi Li, Chong Liu, Yunjian Li, Qingyue Hu, Mazen Elsaid, Bijin Li, Jayabrata Das, Yanfeng Dang, Debabrata Maiti, Haibo Ge
Abstract
palladium catalysis. However, the current techniques are restricted to terminal methyl functionalization, limiting their structural scopes and applicability. Herein, we report the development of a direct Pd-catalyzed methylene β-C-H arylation of linear unmasked aldehydes by using 3-amino-3-methylbutanoic acid as a TDG and 2-pyridone as an external ligand. Density functional theory calculations provided insights into the reaction mechanism and shed light on the roles of the external and transient directing ligands in the catalytic transformation.
Topics & Concepts
CatalysisPalladiumChemistryLigand (biochemistry)Surface modificationMethyleneCombinatorial chemistryLimitingMedicinal chemistryOrganic chemistryReceptorBiochemistryMechanical engineeringPhysical chemistryEngineeringCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSynthesis and Catalytic Reactions