General Synthesis of Chiral α,α-Diaryl Carboxamides by Enantioselective Palladium-Catalyzed Cross-Coupling
Bowen Li, Muinat A. Aliyu, Zhenhua Gao, Tiejun Li, Dong Wei, Junchen Li, Enxue Shi, Wenjun Tang
Abstract
A general synthesis of chiral α,α-diaryl carboxamides is developed by enantioselective cross-coupling between 2-bromo-2-aryl carboxamides and arylboronic acids, leading to a series of chiral α,α-diaryl carboxamides with various electronic properties and functionalities in moderate to excellent enantioselectivities and yields. The employment of a sterically bulky chiral P,P═O ligand L2 is critical for the reactivity and selectivity. This protocol is applied to an efficient asymmetric synthesis of a key intermediate of dopamine receptor agonist SKF 38393.
Topics & Concepts
ChemistryEnantioselective synthesisSteric effectsPalladiumCatalysisLigand (biochemistry)AgonistChiral ligandArylCombinatorial chemistrySelectivityReactivity (psychology)StereochemistryReceptorOrganic chemistryBiochemistryAlkylMedicineAlternative medicinePathologyCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Synthesis and Catalysis