Selective C-H activation of alipathic hydrocarbons under phase-transfer conditions

Peter R. Schreiner, Oliver Lauenstein, Igor V. Kolomitsyn, Suad Nadi, Andrey A. Fokin

Research output: Contribution to journalArticlepeer-review

59 Scopus citations

Abstract

Bromination of alipathic 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 alipathic C-H activation very likely relies on the initiation of single-electron transfer followed by a radical substitution with unusually high regioselectivity.

Original languageEnglish (US)
Pages (from-to)1895-1897
Number of pages3
JournalAngewandte Chemie - International Edition
Volume37
Issue number13-14
DOIs
StatePublished - Aug 3 1998

Keywords

  • Adamantane
  • C-H activation
  • Phase-transfer catalysis
  • Radicals
  • Single-electron transfer

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