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 Zhdankin

doi:10.1002/adsc.200800784

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 Zhdankin

Chemistry & Biochemistry

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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 language	English (US)
Pages (from-to)	733-737
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	351
Issue number	5
DOIs	https://doi.org/10.1002/adsc.200800784
State	Published - Mar 2009

Keywords

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

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10.1002/adsc.200800784

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Geraskin, I. M., Pavlova, O., Neu, H. M., Yusubov, M. S., Nemykin, V. N., & Zhdankin, V. (2009). 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. Advanced Synthesis and Catalysis, 351(5), 733-737. https://doi.org/10.1002/adsc.200800784

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. / Geraskin, Ivan M.; Pavlova, Olga; Neu, Heather M. et al.
In: Advanced Synthesis and Catalysis, Vol. 351, No. 5, 03.2009, p. 733-737.

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

Geraskin, IM, Pavlova, O, Neu, HM, Yusubov, MS, Nemykin, VN & Zhdankin, V 2009, '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', Advanced Synthesis and Catalysis, vol. 351, no. 5, pp. 733-737. https://doi.org/10.1002/adsc.200800784

Geraskin IM, Pavlova O, Neu HM, Yusubov MS, Nemykin VN, Zhdankin V. 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. Advanced Synthesis and Catalysis. 2009 Mar;351(5):733-737. doi: 10.1002/adsc.200800784

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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 Viktor Zhdankin",

year = "2009",

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doi = "10.1002/adsc.200800784",

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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.

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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.

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KW - Iodosylbenzene

KW - Oxygenation, porphyrins

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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

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Keywords

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