Nickel‐Catalyzed Stereo‐ and Enantioselective Cross‐Coupling of <i>gem</i>‐Difluoroalkenes with Carbon Electrophiles by C−F Bond Activation
Ziqi Zhu, Lin Lin, Jieshuai Xiao, Zhuangzhi Shi
Abstract
Abstract Stereo‐ and enantioselective cross‐electrophile coupling involving C−F bond activation is reported. Treatment of gem‐difluoroalkenes with racemic benzyl electrophiles in the presence of a chiral nickel complex using B 2 pin 2 as a stoichiometric reductant allows the construction of a C(sp 2 )−C(sp 3 ) bond under mild conditions, affording a broad range of monofluoroalkenes bearing stereogenic allylic centers. Initial mechanistic studies indicate that a radical chain pathway may be operating, wherein the ester group in the gem‐difluoroalkene promotes C−F bond activation through oxidative addition to a Ni species .
Topics & Concepts
ElectrophileNickelCatalysisEnantioselective synthesisChemistryCoupling (piping)Carbon fibersCoupling reactionCombinatorial chemistryMedicinal chemistryPolymer chemistryOrganic chemistryMaterials scienceMetallurgyComposite numberComposite materialFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods