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Selective C-H Activation of Aliphatic Hydrocarbons under Phase-Transfer Conditions
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1998
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Tertiary BromideChemical EngineeringEngineeringChemical TransformationBiochemistryNatural SciencesOrganic ChemistrySelective C-h ActivationNew SystemReaction IntermediatePolycyclic Aromatic HydrocarbonHydrogenChemistrySecondary BondHalogenationChemical KineticsEnantioselective Synthesis
Bromination of aliphatic hydrocarbons with NaOH/CBr4 under phase-transfer conditions selectively gives the tertiary bromide. In the absence of a tertiary C–H bond in the molecule, a secondary bond will be activated (see reaction equation). This conceptionally new system for aliphatic C–H activation very likely relies on the initiation of single-electron transfer followed by a radical substitution with unusually high regioselectivity.