Iodine(V)/ruthenium(III)-cocatalyzed oxidations: A highly efficient tandem catalytic system for the oxidation of alcohols and hydrocarbons with oxone

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Abstract

An extremely mild and efficient tandem catalytic system for the oxidation of alcohols and hydrocarbons based on Ru(III)-catalyzed reoxidation of ArIO to ArIO2 was reported, by using Oxone as a stoichiometric oxidant. Oxone was added to a mixture of propylbenzene, PhI, and RuCl3 in acetonitrile and water in five portions over 22 h under stirring at room temperature. The reaction mixture was stirred for an additional 4 h and was monitored by TLC by the disappearance of propylbenzene. Then ethyl acetate and water were added and the mixture was stirred for 5 mm. The organic solution was separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with NaCl, and dried over Na2SO 4. The oxidation of the other hydrocarbons was performed by using a similar procedure. The use of smaller amounts of Oxone led to incomplete conversion owing to its noticeable decomposition with loss of oxygen gas under reaction conditions.

Original languageEnglish
Pages (from-to)11091-11094
Number of pages4
JournalChemistry - A European Journal
Volume15
Issue number42
DOIs
Publication statusPublished - 26 Oct 2009

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Ruthenium
Hydrocarbons
Iodine
Alcohols
Oxidation
Water
Acetonitrile
Oxidants
Gases
Oxygen
Decomposition
potassium peroxymonosulfuric acid
Temperature
n-propylbenzene
ethyl acetate

Keywords

  • Catalysis
  • Hypervalent compounds
  • Oxidation
  • Oxone
  • Ruthenium

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Iodine(V)/ruthenium(III)-cocatalyzed oxidations: A highly efficient tandem catalytic system for the oxidation of alcohols and hydrocarbons with oxone",
abstract = "An extremely mild and efficient tandem catalytic system for the oxidation of alcohols and hydrocarbons based on Ru(III)-catalyzed reoxidation of ArIO to ArIO2 was reported, by using Oxone as a stoichiometric oxidant. Oxone was added to a mixture of propylbenzene, PhI, and RuCl3 in acetonitrile and water in five portions over 22 h under stirring at room temperature. The reaction mixture was stirred for an additional 4 h and was monitored by TLC by the disappearance of propylbenzene. Then ethyl acetate and water were added and the mixture was stirred for 5 mm. The organic solution was separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with NaCl, and dried over Na2SO 4. The oxidation of the other hydrocarbons was performed by using a similar procedure. The use of smaller amounts of Oxone led to incomplete conversion owing to its noticeable decomposition with loss of oxygen gas under reaction conditions.",
keywords = "Catalysis, Hypervalent compounds, Oxidation, Oxone, Ruthenium",
author = "Yusubov, {Mekhman S.} and Zagulyaeva, {Aleksandra A.} and Zhdankin, {Viktor Vladimirovich}",
year = "2009",
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T2 - A highly efficient tandem catalytic system for the oxidation of alcohols and hydrocarbons with oxone

AU - Yusubov, Mekhman S.

AU - Zagulyaeva, Aleksandra A.

AU - Zhdankin, Viktor Vladimirovich

PY - 2009/10/26

Y1 - 2009/10/26

N2 - An extremely mild and efficient tandem catalytic system for the oxidation of alcohols and hydrocarbons based on Ru(III)-catalyzed reoxidation of ArIO to ArIO2 was reported, by using Oxone as a stoichiometric oxidant. Oxone was added to a mixture of propylbenzene, PhI, and RuCl3 in acetonitrile and water in five portions over 22 h under stirring at room temperature. The reaction mixture was stirred for an additional 4 h and was monitored by TLC by the disappearance of propylbenzene. Then ethyl acetate and water were added and the mixture was stirred for 5 mm. The organic solution was separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with NaCl, and dried over Na2SO 4. The oxidation of the other hydrocarbons was performed by using a similar procedure. The use of smaller amounts of Oxone led to incomplete conversion owing to its noticeable decomposition with loss of oxygen gas under reaction conditions.

AB - An extremely mild and efficient tandem catalytic system for the oxidation of alcohols and hydrocarbons based on Ru(III)-catalyzed reoxidation of ArIO to ArIO2 was reported, by using Oxone as a stoichiometric oxidant. Oxone was added to a mixture of propylbenzene, PhI, and RuCl3 in acetonitrile and water in five portions over 22 h under stirring at room temperature. The reaction mixture was stirred for an additional 4 h and was monitored by TLC by the disappearance of propylbenzene. Then ethyl acetate and water were added and the mixture was stirred for 5 mm. The organic solution was separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with NaCl, and dried over Na2SO 4. The oxidation of the other hydrocarbons was performed by using a similar procedure. The use of smaller amounts of Oxone led to incomplete conversion owing to its noticeable decomposition with loss of oxygen gas under reaction conditions.

KW - Catalysis

KW - Hypervalent compounds

KW - Oxidation

KW - Oxone

KW - Ruthenium

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