Binuclear iron(III) phthalocyanine(μ-oxodimer)-catalyzed oxygenation of aromatic hydrocarbons with iodosylbenzene sulfate and iodosylbenzene as the oxidants

Abstract

Two binuclear iron(III) phthalocyanine-(μ-oxodimer) complexes were tested in catalytic oxygenation reactions of several aromatic hydrocarbons using iodosylbenzene (PhIO)_n or oligomeric iodosylbenzene sulfate [(PhIO)₃SO₃]_n as the oxidants. Results of this study demonstrate that [(PhIO)₃SO₃]_n is the most reactive oxygenating reagent that can be used as a safe and convenient alternative to the thermally unstable and potentially explosive iodosylbenzene. The pyridine-containing binuclear μ-oxobis-{iron(III)-pyridino[3,4]-9(10), 16(17),23(24)-tri-tertbutyltribenzoporphyrazine} is significantly more active as compared to the traditional μ-oxobis[iron-(III)-2,9(10),16(17),23(24)-tetra- tert-butylphthalocyanine].

Original language	English
Pages (from-to)	3168-3174
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	351
Issue number	18
DOIs	https://doi.org/10.1002/adsc.200900705
Publication status	Published - Dec 2009

Keywords

Iodine
Iodosylbenzene
Iodosylbenzene sulfate
Iron phthalocyanine μ-oxodimer
Oxygenation

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200900705

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Binuclear iron(III) phthalocyanine(μ-oxodimer)-catalyzed oxygenation of aromatic hydrocarbons with iodosylbenzene sulfate and iodosylbenzene as the oxidants. / Neu, Heather M.; Yusubov, Mekhman S.; Zhdankin, Viktor Vladimirovich; Nemykin, Victor N.

In: Advanced Synthesis and Catalysis, Vol. 351, No. 18, 12.2009, p. 3168-3174.

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

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title = "Binuclear iron(III) phthalocyanine(μ-oxodimer)-catalyzed oxygenation of aromatic hydrocarbons with iodosylbenzene sulfate and iodosylbenzene as the oxidants",

abstract = "Two binuclear iron(III) phthalocyanine-(μ-oxodimer) complexes were tested in catalytic oxygenation reactions of several aromatic hydrocarbons using iodosylbenzene (PhIO)n or oligomeric iodosylbenzene sulfate [(PhIO)3SO3]n as the oxidants. Results of this study demonstrate that [(PhIO)3SO3]n is the most reactive oxygenating reagent that can be used as a safe and convenient alternative to the thermally unstable and potentially explosive iodosylbenzene. The pyridine-containing binuclear μ-oxobis-{iron(III)-pyridino[3,4]-9(10), 16(17),23(24)-tri-tertbutyltribenzoporphyrazine} is significantly more active as compared to the traditional μ-oxobis[iron-(III)-2,9(10),16(17),23(24)-tetra- tert-butylphthalocyanine].",

keywords = "Iodine, Iodosylbenzene, Iodosylbenzene sulfate, Iron phthalocyanine μ-oxodimer, Oxygenation",

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

year = "2009",

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doi = "10.1002/adsc.200900705",

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AU - Neu, Heather M.

AU - Yusubov, Mekhman S.

AU - Zhdankin, Viktor Vladimirovich

AU - Nemykin, Victor N.

PY - 2009/12

Y1 - 2009/12

N2 - Two binuclear iron(III) phthalocyanine-(μ-oxodimer) complexes were tested in catalytic oxygenation reactions of several aromatic hydrocarbons using iodosylbenzene (PhIO)n or oligomeric iodosylbenzene sulfate [(PhIO)3SO3]n as the oxidants. Results of this study demonstrate that [(PhIO)3SO3]n is the most reactive oxygenating reagent that can be used as a safe and convenient alternative to the thermally unstable and potentially explosive iodosylbenzene. The pyridine-containing binuclear μ-oxobis-{iron(III)-pyridino[3,4]-9(10), 16(17),23(24)-tri-tertbutyltribenzoporphyrazine} is significantly more active as compared to the traditional μ-oxobis[iron-(III)-2,9(10),16(17),23(24)-tetra- tert-butylphthalocyanine].

AB - Two binuclear iron(III) phthalocyanine-(μ-oxodimer) complexes were tested in catalytic oxygenation reactions of several aromatic hydrocarbons using iodosylbenzene (PhIO)n or oligomeric iodosylbenzene sulfate [(PhIO)3SO3]n as the oxidants. Results of this study demonstrate that [(PhIO)3SO3]n is the most reactive oxygenating reagent that can be used as a safe and convenient alternative to the thermally unstable and potentially explosive iodosylbenzene. The pyridine-containing binuclear μ-oxobis-{iron(III)-pyridino[3,4]-9(10), 16(17),23(24)-tri-tertbutyltribenzoporphyrazine} is significantly more active as compared to the traditional μ-oxobis[iron-(III)-2,9(10),16(17),23(24)-tetra- tert-butylphthalocyanine].

KW - Iodine

KW - Iodosylbenzene

KW - Iodosylbenzene sulfate

KW - Iron phthalocyanine μ-oxodimer

KW - Oxygenation

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