Selective C–H Activation of Aliphatic Hydrocarbons under Phase??Transfer Conditions

…, O Lauenstein, IV Kolomitsyn, S Nadi…

Index: Schreiner, Peter R.; Lauenstein, Oliver; Kolomitsyn, Igor V.; Nadi, Suad; Fokin, Andrey A. Angewandte Chemie - International Edition, 1998 , vol. 37, # 13-14 p. 1895 - 1897

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Citation Number: 57

Abstract

Abstract Bromination of aliphatic hydrocarbons with NaOH/CBr 4 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.

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