Design and Synthesis of TY‐Phos and Application in Palladium‐Catalyzed Enantioselective Fluoroarylation of<i>gem</i>‐Difluoroalkenes
Tao‐Yan Lin, Zhangjin Pan, Youshao Tu, Shuai Zhu, Haihong Wu, Yu Liu, Zhiming Li, Junliang Zhang
Abstract
Abstract The first example of highly enantioselective fluoroarylation of gem‐difluoroalkenes with aryl halides is presented by using a new chiral sulfinamide phosphine ( Sadphos ) type ligand TY‐Phos . N‐Me‐ TY‐Phos can be easily synthesized on a gram scale from readily available starting materials in three steps. Salient features of this work including readily available starting materials, good yields, high enantioselectivities as well as broad substrate scope make this approach very practical and attractive. Notably, the asymmetric synthesis of an analogue of a biologically active molecule is also reported.
Topics & Concepts
Enantioselective synthesisCombinatorial chemistryPhosphinePalladiumChemistryPhosArylSubstrate (aquarium)Ligand (biochemistry)CatalysisOrganic chemistryAlkylGeologyReceptorOceanographyBiochemistryFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods