Highly efficient RuCl3-catalyzed disproportionation of (diacetoxyiodo)benzene to iodylbenzene and iodobenzene; leading to the efficient oxidation of alcohols to carbonyl compounds

Mekhman S. Yusubov, Ki Whan Chi, Joo Yeon Park, Rashad Karimov, Viktor Vladimirovich Zhdankin

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49 Citations (Scopus)

Abstract

(Diacetoxyiodo)benzene (DIB) selectively oxidizes primary and secondary alcohols to the respective carbonyl compounds in the presence of RuCl3 (0.8-1.0 mol %) at room temperature in aqueous acetonitrile. This reaction proceeds via an initial instantaneous Ru-catalyzed disproportionation of DIB to iodobenzene and iodylbenzene with the latter acting as the actual stoichiometric oxidant toward alcohols.

Original languageEnglish
Pages (from-to)6305-6308
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number35
DOIs
Publication statusPublished - 28 Aug 2006

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Carbonyl compounds
Benzene
Alcohols
Oxidation
Oxidants
Temperature
iodobenzene
acetonitrile

Keywords

  • (Diacetoxyiodo)benzene
  • Catalysis
  • Hypervalent iodine
  • Iodylbenzene
  • Oxidation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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title = "Highly efficient RuCl3-catalyzed disproportionation of (diacetoxyiodo)benzene to iodylbenzene and iodobenzene; leading to the efficient oxidation of alcohols to carbonyl compounds",
abstract = "(Diacetoxyiodo)benzene (DIB) selectively oxidizes primary and secondary alcohols to the respective carbonyl compounds in the presence of RuCl3 (0.8-1.0 mol {\%}) at room temperature in aqueous acetonitrile. This reaction proceeds via an initial instantaneous Ru-catalyzed disproportionation of DIB to iodobenzene and iodylbenzene with the latter acting as the actual stoichiometric oxidant toward alcohols.",
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author = "Yusubov, {Mekhman S.} and Chi, {Ki Whan} and Park, {Joo Yeon} and Rashad Karimov and Zhdankin, {Viktor Vladimirovich}",
year = "2006",
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T1 - Highly efficient RuCl3-catalyzed disproportionation of (diacetoxyiodo)benzene to iodylbenzene and iodobenzene; leading to the efficient oxidation of alcohols to carbonyl compounds

AU - Yusubov, Mekhman S.

AU - Chi, Ki Whan

AU - Park, Joo Yeon

AU - Karimov, Rashad

AU - Zhdankin, Viktor Vladimirovich

PY - 2006/8/28

Y1 - 2006/8/28

N2 - (Diacetoxyiodo)benzene (DIB) selectively oxidizes primary and secondary alcohols to the respective carbonyl compounds in the presence of RuCl3 (0.8-1.0 mol %) at room temperature in aqueous acetonitrile. This reaction proceeds via an initial instantaneous Ru-catalyzed disproportionation of DIB to iodobenzene and iodylbenzene with the latter acting as the actual stoichiometric oxidant toward alcohols.

AB - (Diacetoxyiodo)benzene (DIB) selectively oxidizes primary and secondary alcohols to the respective carbonyl compounds in the presence of RuCl3 (0.8-1.0 mol %) at room temperature in aqueous acetonitrile. This reaction proceeds via an initial instantaneous Ru-catalyzed disproportionation of DIB to iodobenzene and iodylbenzene with the latter acting as the actual stoichiometric oxidant toward alcohols.

KW - (Diacetoxyiodo)benzene

KW - Catalysis

KW - Hypervalent iodine

KW - Iodylbenzene

KW - Oxidation

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DO - 10.1016/j.tetlet.2006.06.100

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