Regioselective C–H Active Carbonylation via 1,4-Palladium Migration
Ming Li, Shun‐Xi Li, Dong‐Ping Chen, Fan Gao, Yi‐Feng Qiu, Xi‐Cun Wang, Zheng‐Jun Quan, Yong‐Min Liang
Abstract
We report a highly regioselective three-component coupling reaction of styrene, CO gas, and an amine compound to synthesize multisubstituted α,β-unsaturated amides, which involves a palladium-catalyzed sequential 1,4-palladium migration, C(sp 2 )–H activation, carbonylation, and amination. Salient features of this strategy include the use of 1 atm of CO, excellent stereochemistry, and good functional group tolerance. Further, a series of control experiments and density functional theory calculations were performed to afford some insights for the transfer mechanism.
Topics & Concepts
ChemistryRegioselectivityPalladiumCarbonylationAminationFunctional groupStyreneAmine gas treatingCatalysisDensity functional theoryCombinatorial chemistryOrganic chemistryComputational chemistryCarbon monoxideCopolymerPolymerCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAdvanced Synthetic Organic Chemistry