A high performance oxidation method for secondary alcohols by inductive activation of TEMPO in combination with pyridine-bromine complexes

Zhen Wu Mei, Takumi Omote, Mounir Mansour, Hiroyuki Kawafuchi, Yutaka Takaguchi, Anny Jutand*, Sadao Tsuboi, Tsutomu Inokuchi

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

A new TEMPO-mediated catalytic oxidation method in combination with Py·HBr3 (stoichiometric) is developed for oxidation of secondary alcohols to the corresponding ketones. The performance of this oxidizing system is better compared with that of TEMPO method combined with R4NBr3. Poly(4-vinylpyridine)·HBr3 can be used in place of Py·HBr3. The electron-withdrawing substituent at the C-4 position of TEMPO increases the reactivity of TEMPO significantly in the oxidation of electron-deficient alcohols such as polyhaloalkylmethanols. Inductive effect of the substituent of TEMPO is discussed through the characterization of the redox potential of N-O radical by cyclic voltammetry.

Original languageEnglish
Pages (from-to)10761-10766
Number of pages6
JournalTetrahedron
Volume64
Issue number47
DOIs
StatePublished - 2008/11/17

Keywords

  • Co-oxidant
  • Cyclic voltammetry
  • Oxidation
  • Redox
  • TEMPO

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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