m-iodosylbenzoic acid as a convenient recyclable reagent for highly efficient RuCl3-catalyzed oxidation of alcohols to carbonyl compounds

Mekhman S. Yusubov; Marina P. Gilmkhanova; Viktor V. Zhdankin; Andreas Kirschning

doi:10.1055/s-2007-970742

m-iodosylbenzoic acid as a convenient recyclable reagent for highly efficient RuCl₃-catalyzed oxidation of alcohols to carbonyl compounds

Mekhman S. Yusubov, Marina P. Gilmkhanova, Viktor V. Zhdankin, Andreas Kirschning

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

m-Iodosylbenzoic acid selectively oxidizes primary and secondary alcohols to the respective carbonyl compounds in the presence of RuCl₃ (0.5 mol%) at room temperature in aqueous acetonitrile. Separation of pure products is conveniently achieved by scavenging any aryl iodide by ion exchange with IRA-900 (hydroxide form) or by simple extraction of the basic aqueous solution with water. The reduced form of the reagent, m-iodobenzoic acid, can be easily recovered from the ion-exchange resin or from the basic aqueous solution by simple acidification with HCl.

Original language	English (US)
Pages (from-to)	563-566
Number of pages	4
Journal	Synlett
Issue number	4
DOIs	https://doi.org/10.1055/s-2007-970742
State	Published - Mar 1 2007

Keywords

Catalysis
Hypervalent iodine
Oxidation
Scavenger
m-iodosobenzoic acid

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Cite this

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T1 - m-iodosylbenzoic acid as a convenient recyclable reagent for highly efficient RuCl3-catalyzed oxidation of alcohols to carbonyl compounds

AU - Yusubov, Mekhman S.

AU - Gilmkhanova, Marina P.

AU - Zhdankin, Viktor V.

AU - Kirschning, Andreas

PY - 2007/3/1

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N2 - m-Iodosylbenzoic acid selectively oxidizes primary and secondary alcohols to the respective carbonyl compounds in the presence of RuCl3 (0.5 mol%) at room temperature in aqueous acetonitrile. Separation of pure products is conveniently achieved by scavenging any aryl iodide by ion exchange with IRA-900 (hydroxide form) or by simple extraction of the basic aqueous solution with water. The reduced form of the reagent, m-iodobenzoic acid, can be easily recovered from the ion-exchange resin or from the basic aqueous solution by simple acidification with HCl.

AB - m-Iodosylbenzoic acid selectively oxidizes primary and secondary alcohols to the respective carbonyl compounds in the presence of RuCl3 (0.5 mol%) at room temperature in aqueous acetonitrile. Separation of pure products is conveniently achieved by scavenging any aryl iodide by ion exchange with IRA-900 (hydroxide form) or by simple extraction of the basic aqueous solution with water. The reduced form of the reagent, m-iodobenzoic acid, can be easily recovered from the ion-exchange resin or from the basic aqueous solution by simple acidification with HCl.

KW - Catalysis

KW - Hypervalent iodine

KW - Oxidation

KW - Scavenger

KW - m-iodosobenzoic acid

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