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

doi:10.1016/j.tet.2008.08.051

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

Materials Design and Engineering

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	10761-10766
Number of pages	6
Journal	Tetrahedron
Volume	64
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2008.08.051
State	Published - 2008/11/17

Keywords

Co-oxidant
Cyclic voltammetry
Oxidation
Redox
TEMPO

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2008.08.051

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@article{6e268be4792640eab1a287e3d8bd7d23,

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

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.",

keywords = "Co-oxidant, Cyclic voltammetry, Oxidation, Redox, TEMPO",

author = "Mei, {Zhen Wu} and Takumi Omote and Mounir Mansour and Hiroyuki Kawafuchi and Yutaka Takaguchi and Anny Jutand and Sadao Tsuboi and Tsutomu Inokuchi",

note = "Funding Information: Financial supports by Electric Technology Research Foundation of Chugoku and the Okayama Foundation for Science and Technology are gratefully acknowledged. Z.-W.M. thanks Wesco Scientific Promotion Foundation for scholarship. We are thankful to {\textquoteleft}SC-NMR laboratory of Okayama University{\textquoteright} for high-field NMR experiments and to Professor Junzo Nokami, Okayama University of Science, for HRMS analyses. ",

year = "2008",

month = nov,

day = "17",

doi = "10.1016/j.tet.2008.08.051",

language = "英語",

volume = "64",

pages = "10761--10766",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "47",

}

TY - JOUR

T1 - A high performance oxidation method for secondary alcohols by inductive activation of TEMPO in combination with pyridine-bromine complexes

AU - Mei, Zhen Wu

AU - Omote, Takumi

AU - Mansour, Mounir

AU - Kawafuchi, Hiroyuki

AU - Takaguchi, Yutaka

AU - Jutand, Anny

AU - Tsuboi, Sadao

AU - Inokuchi, Tsutomu

N1 - Funding Information: Financial supports by Electric Technology Research Foundation of Chugoku and the Okayama Foundation for Science and Technology are gratefully acknowledged. Z.-W.M. thanks Wesco Scientific Promotion Foundation for scholarship. We are thankful to ‘SC-NMR laboratory of Okayama University’ for high-field NMR experiments and to Professor Junzo Nokami, Okayama University of Science, for HRMS analyses.

PY - 2008/11/17

Y1 - 2008/11/17

N2 - 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.

AB - 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.

KW - Co-oxidant

KW - Cyclic voltammetry

KW - Oxidation

KW - Redox

KW - TEMPO

UR - http://www.scopus.com/inward/record.url?scp=53149131670&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2008.08.051

DO - 10.1016/j.tet.2008.08.051

M3 - 学術論文

AN - SCOPUS:53149131670

SN - 0040-4020

VL - 64

SP - 10761

EP - 10766

JO - Tetrahedron

JF - Tetrahedron

IS - 47

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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