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

Research output: Contribution to journalArticle

26 Citations (Scopus)

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
Publication statusPublished - Nov 17 2008

Fingerprint

Bromine
Chemical activation
Alcohols
Oxidation
Electrons
Catalytic oxidation
Ketones
Cyclic voltammetry
Oxidation-Reduction
pyridine
TEMPO

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A high performance oxidation method for secondary alcohols by inductive activation of TEMPO in combination with pyridine-bromine complexes. / Mei, Zhen Wu; Omote, Takumi; Mansour, Mounir; Kawafuchi, Hiroyuki; Takaguchi, Yutaka; Jutand, Anny; Tsuboi, Sadao; Inokuchi, Tsutomu.

In: Tetrahedron, Vol. 64, No. 47, 17.11.2008, p. 10761-10766.

Research output: Contribution to journalArticle

Mei, Zhen Wu ; Omote, Takumi ; Mansour, Mounir ; Kawafuchi, Hiroyuki ; Takaguchi, Yutaka ; Jutand, Anny ; Tsuboi, Sadao ; Inokuchi, Tsutomu. / A high performance oxidation method for secondary alcohols by inductive activation of TEMPO in combination with pyridine-bromine complexes. In: Tetrahedron. 2008 ; Vol. 64, No. 47. pp. 10761-10766.
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AU - Takaguchi, Yutaka

AU - Jutand, Anny

AU - Tsuboi, Sadao

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