Comparative reactivity of hypervalent iodine oxidants in metalloporphyrin-catalyzed oxygenation of hydrocarbons

Iodosylbenzene sulfate and 2-iodylbenzoic acid ester as safe and convenient alternatives to iodosylbenzene

Ivan M. Geraskin, Olga Pavlova, Heather M. Neu, Mekhman S. Yusubov, Victor N. Nemykin, Viktor Vladimirovich Zhdankin

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

A comparative study of the reactivity of 2-iodylbenzoic acid isopropyl ester (IBX-ester), oligomeric iodosylbenzene sulfate [(PhIO)3· SO3]u, and iodosylbenzene in the oxygenation of anthracene in the presence of metal porphyrin or phthalocyanine complexes is reported. Results of this study demonstrate that oligomeric iodosylbenzene sulfate and the IBX-ester are the most reactive oxygenating reagents that can be used as a safe and convenient alternative to the thermally unstable and potentially explosive iodosylbenzene.

Original languageEnglish
Pages (from-to)733-737
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume351
Issue number5
DOIs
Publication statusPublished - Mar 2009

Fingerprint

Metalloporphyrins
Oxygenation
Hydrocarbons
Iodine
Oxidants
Sulfates
Esters
Acids
Anthracene
Porphyrins
Metals
iodosobenzene

Keywords

  • 2-iodylbenzoic acid isopropyl ester (IBX-ester)
  • Iodine
  • Iodosylbenzene
  • Oxygenation, porphyrins

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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title = "Comparative reactivity of hypervalent iodine oxidants in metalloporphyrin-catalyzed oxygenation of hydrocarbons: Iodosylbenzene sulfate and 2-iodylbenzoic acid ester as safe and convenient alternatives to iodosylbenzene",
abstract = "A comparative study of the reactivity of 2-iodylbenzoic acid isopropyl ester (IBX-ester), oligomeric iodosylbenzene sulfate [(PhIO)3· SO3]u, and iodosylbenzene in the oxygenation of anthracene in the presence of metal porphyrin or phthalocyanine complexes is reported. Results of this study demonstrate that oligomeric iodosylbenzene sulfate and the IBX-ester are the most reactive oxygenating reagents that can be used as a safe and convenient alternative to the thermally unstable and potentially explosive iodosylbenzene.",
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author = "Geraskin, {Ivan M.} and Olga Pavlova and Neu, {Heather M.} and Yusubov, {Mekhman S.} and Nemykin, {Victor N.} and Zhdankin, {Viktor Vladimirovich}",
year = "2009",
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T1 - Comparative reactivity of hypervalent iodine oxidants in metalloporphyrin-catalyzed oxygenation of hydrocarbons

T2 - Iodosylbenzene sulfate and 2-iodylbenzoic acid ester as safe and convenient alternatives to iodosylbenzene

AU - Geraskin, Ivan M.

AU - Pavlova, Olga

AU - Neu, Heather M.

AU - Yusubov, Mekhman S.

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor Vladimirovich

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N2 - A comparative study of the reactivity of 2-iodylbenzoic acid isopropyl ester (IBX-ester), oligomeric iodosylbenzene sulfate [(PhIO)3· SO3]u, and iodosylbenzene in the oxygenation of anthracene in the presence of metal porphyrin or phthalocyanine complexes is reported. Results of this study demonstrate that oligomeric iodosylbenzene sulfate and the IBX-ester are the most reactive oxygenating reagents that can be used as a safe and convenient alternative to the thermally unstable and potentially explosive iodosylbenzene.

AB - A comparative study of the reactivity of 2-iodylbenzoic acid isopropyl ester (IBX-ester), oligomeric iodosylbenzene sulfate [(PhIO)3· SO3]u, and iodosylbenzene in the oxygenation of anthracene in the presence of metal porphyrin or phthalocyanine complexes is reported. Results of this study demonstrate that oligomeric iodosylbenzene sulfate and the IBX-ester are the most reactive oxygenating reagents that can be used as a safe and convenient alternative to the thermally unstable and potentially explosive iodosylbenzene.

KW - 2-iodylbenzoic acid isopropyl ester (IBX-ester)

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