Selective C-H Activation of Aliphatic Hydrocarbons under Phase-Transfer Conditions

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.