Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species

Mekhman S. Yusubov; Victor N. Nemykin; Viktor Zhdankin

doi:10.1016/j.tet.2010.04.046

Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species

Mekhman S. Yusubov, Victor N. Nemykin, Viktor Zhdankin

Chemistry & Biochemistry

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

79 Scopus citations

Abstract

Several transition metal-mediated oxidations using hypervalent iodine species are reported. A convenient procedure for preparation of iodylarenes via RuCl₃-catalyzed oxidation of iodoarenes has been developed. This procedure allows the generation of highly reactive monomeric iodine(V) species, which are excellent oxidants toward alcohols and hydrocarbons in situ. A broad range of substrates can be oxidized to carbonyl compounds by a tandem catalytic system based on the Ru(III)-catalyzed reoxidation of ArIO to ArIO₂ using Oxone^® as oxidant. It was shown that electrophilic iodine(III) species, originating from oligomeric iodosylbenzene sulfate (PhIO)₃SO₃, are efficient oxygenating agents in catalytic oxidation of aromatic hydrocarbons in the presence of metalloporphyrin complexes.

Original language	English (US)
Pages (from-to)	5745-5752
Number of pages	8
Journal	Tetrahedron
Volume	66
Issue number	31
DOIs	https://doi.org/10.1016/j.tet.2010.04.046
State	Published - Jul 31 2010

Bibliographical note

Funding Information:
This work was supported by research grants from the National Science Foundation (CHE-1009038) (VVZ) and Petroleum Research Fund, administered by the American Chemical Society (VNN).

Keywords

Catalysis
Hypervalent iodine
Oxidation
Porphyrins
Ruthenium

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10.1016/j.tet.2010.04.046

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title = "Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species",

abstract = "Several transition metal-mediated oxidations using hypervalent iodine species are reported. A convenient procedure for preparation of iodylarenes via RuCl3-catalyzed oxidation of iodoarenes has been developed. This procedure allows the generation of highly reactive monomeric iodine(V) species, which are excellent oxidants toward alcohols and hydrocarbons in situ. A broad range of substrates can be oxidized to carbonyl compounds by a tandem catalytic system based on the Ru(III)-catalyzed reoxidation of ArIO to ArIO2 using Oxone{\textregistered} as oxidant. It was shown that electrophilic iodine(III) species, originating from oligomeric iodosylbenzene sulfate (PhIO)3SO3, are efficient oxygenating agents in catalytic oxidation of aromatic hydrocarbons in the presence of metalloporphyrin complexes.",

keywords = "Catalysis, Hypervalent iodine, Oxidation, Porphyrins, Ruthenium",

author = "Yusubov, {Mekhman S.} and Nemykin, {Victor N.} and Viktor Zhdankin",

note = "Funding Information: This work was supported by research grants from the National Science Foundation (CHE-1009038) (VVZ) and Petroleum Research Fund, administered by the American Chemical Society (VNN). ",

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doi = "10.1016/j.tet.2010.04.046",

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T1 - Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species

AU - Yusubov, Mekhman S.

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor

N1 - Funding Information: This work was supported by research grants from the National Science Foundation (CHE-1009038) (VVZ) and Petroleum Research Fund, administered by the American Chemical Society (VNN).

PY - 2010/7/31

Y1 - 2010/7/31

N2 - Several transition metal-mediated oxidations using hypervalent iodine species are reported. A convenient procedure for preparation of iodylarenes via RuCl3-catalyzed oxidation of iodoarenes has been developed. This procedure allows the generation of highly reactive monomeric iodine(V) species, which are excellent oxidants toward alcohols and hydrocarbons in situ. A broad range of substrates can be oxidized to carbonyl compounds by a tandem catalytic system based on the Ru(III)-catalyzed reoxidation of ArIO to ArIO2 using Oxone® as oxidant. It was shown that electrophilic iodine(III) species, originating from oligomeric iodosylbenzene sulfate (PhIO)3SO3, are efficient oxygenating agents in catalytic oxidation of aromatic hydrocarbons in the presence of metalloporphyrin complexes.

AB - Several transition metal-mediated oxidations using hypervalent iodine species are reported. A convenient procedure for preparation of iodylarenes via RuCl3-catalyzed oxidation of iodoarenes has been developed. This procedure allows the generation of highly reactive monomeric iodine(V) species, which are excellent oxidants toward alcohols and hydrocarbons in situ. A broad range of substrates can be oxidized to carbonyl compounds by a tandem catalytic system based on the Ru(III)-catalyzed reoxidation of ArIO to ArIO2 using Oxone® as oxidant. It was shown that electrophilic iodine(III) species, originating from oligomeric iodosylbenzene sulfate (PhIO)3SO3, are efficient oxygenating agents in catalytic oxidation of aromatic hydrocarbons in the presence of metalloporphyrin complexes.

KW - Catalysis

KW - Hypervalent iodine

KW - Oxidation

KW - Porphyrins

KW - Ruthenium

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DO - 10.1016/j.tet.2010.04.046

M3 - Article

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SN - 0040-4020

VL - 66

SP - 5745

EP - 5752

JO - Tetrahedron

JF - Tetrahedron

IS - 31

ER -

Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species

Abstract

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Keywords

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