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Palladium‐Catalyzed Intermolecular Dicarbofunctionalization of Unactivated Alkenes: Synthesis of Fluoroalkylated Heterocycles with All‐Carbon Quaternary Centers
15
Citations
78
References
2021
Year
Chemical EngineeringCross-coupling ReactionLow TemperaturesFluoroalkylated HeterocyclesEngineeringAlkene MetathesisNatural SciencesDiversity-oriented SynthesisOperative Radical MechanismAll‐carbon Quaternary CentersOrganic ChemistryDual PhosphineOrganometallic CatalysisCatalysisChemistryPalladium‐catalyzed Intermolecular Dicarbofunctionalization
Abstract The redox‐neutral palladium‐catalyzed dicarbofunctionalization of unactivated alkenes with a variety of functionalized difluoromethyl and perfluoroalkyl halide is presented here. This transformation proceeds smoothly at low temperatures and enables the assembly of diversified fluoroalkylated pyrrolo[1,2‐a]indole derivatives with one all‐carbon quaternary center in high regioselectivity. Mechanistic studies suggested an operative radical mechanism and the initiation of the inner‐sphere single electron transfer between a dual phosphine ligand‐coordinated palladium(0) species and perfluoroalkyl halides.
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