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 Zhdankin

doi:10.1016/j.tetlet.2006.06.100

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 Zhdankin

Chemistry & Biochemistry

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

54 Scopus citations

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 language	English (US)
Pages (from-to)	6305-6308
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2006.06.100
State	Published - Aug 28 2006

Bibliographical note

Funding Information:
The authors gratefully acknowledge the National Science Foundation for support of this work through research Grant (CHE 0353541), NSF-MRI award (CHE 0416157) and University of Ulsan Research Fund 2006.

Keywords

(Diacetoxyiodo)benzene
Catalysis
Hypervalent iodine
Iodylbenzene
Oxidation

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10.1016/j.tetlet.2006.06.100

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Highly efficient RuCl₃-catalyzed disproportionation of (diacetoxyiodo)benzene to iodylbenzene and iodobenzene; leading to the efficient oxidation of alcohols to carbonyl compounds. / Yusubov, Mekhman S.; Chi, Ki Whan; Park, Joo Yeon et al.
In: Tetrahedron Letters, Vol. 47, No. 35, 28.08.2006, p. 6305-6308.

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

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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.",

keywords = "(Diacetoxyiodo)benzene, Catalysis, Hypervalent iodine, Iodylbenzene, Oxidation",

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note = "Funding Information: The authors gratefully acknowledge the National Science Foundation for support of this work through research Grant (CHE 0353541), NSF-MRI award (CHE 0416157) and University of Ulsan Research Fund 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

N1 - Funding Information: The authors gratefully acknowledge the National Science Foundation for support of this work through research Grant (CHE 0353541), NSF-MRI award (CHE 0416157) and University of Ulsan Research Fund 2006.

PY - 2006/8/28

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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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