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

Heather M. Neu, Mekhman S. Yusubov, Viktor Vladimirovich Zhdankin, Victor N. Nemykin

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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 languageEnglish
Pages (from-to)3168-3174
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume351
Issue number18
DOIs
Publication statusPublished - Dec 2009

Fingerprint

Aromatic Hydrocarbons
Oxygenation
Aromatic hydrocarbons
Oxidants
Sulfates
Iron
Pyridine
phthalocyanine
iodosobenzene

Keywords

  • Iodine
  • Iodosylbenzene
  • Iodosylbenzene sulfate
  • Iron phthalocyanine μ-oxodimer
  • Oxygenation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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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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pages = "3168--3174",
journal = "Journal fur Praktische Chemie",
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T1 - Binuclear iron(III) phthalocyanine(μ-oxodimer)-catalyzed oxygenation of aromatic hydrocarbons with iodosylbenzene sulfate and iodosylbenzene as the oxidants

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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