Hybrid Palladium Catalyst Assembled from Chiral Phosphoric Acid and Thioamide for Enantioselective β‐C(sp<sup>3</sup>)−H Arylation
Hua‐Jie Jiang, Xiu‐Mei Zhong, Ziye Liu, Rui‐Long Geng, Yangyang Li, Yun‐Dong Wu, Xinhao Zhang, Liu‐Zhu Gong
Abstract
Abstract A hybrid palladium catalyst assembled from a chiral phosphoric acid (CPA) and thioamide enables a highly efficient and enantioselective β‐C(sp 3 )−H functionalization of thioamides (up to 99 % yield, 97 % ee ). A kinetic resolution of unsymmetrical thioamides by intermolecular C(sp 3 )−H arylation can be achieved with high s‐factors. Mechanistic investigations have revealed that stereocontrol is achieved by embedding the substrate in a robust chiral cavity defined by the bulky CPA and a neutral thioamide ligand.
Topics & Concepts
ThioamidePalladiumEnantioselective synthesisChemistryCatalysisPhosphoric acidKinetic resolutionYield (engineering)Substrate (aquarium)Ligand (biochemistry)Combinatorial chemistryOrganic chemistryStereochemistryMedicinal chemistryMaterials scienceBiochemistryGeologyMetallurgyOceanographyReceptorCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSynthetic Organic Chemistry Methods