M-iodosylbenzoic acid as a convenient recyclable hypervalent iodine oxidant for the synthesis of α-iodo ketones by oxidative iodination of ketones

Mehman S. Yusubov, Rosa Y. Yusubova, Tatyana V. Funk, Ki Whan Chi, Andreas Kirschning, Viktor Vladimirovich Zhdankin

Результат исследований: Материалы для журналаСтатья

21 Цитирования (Scopus)

Выдержка

A convenient procedure for the preparation of -iodo ketones by oxidative iodination of ketones using iodine and m-iodosylbenzoic acid as a recyclable hypervalent iodine oxidant is reported. Various ketones and -dicarbonyl compounds can be iodinated by this reagent system under mild conditions affording the respective -iodo-substituted carbonyl compounds in excellent yields. The final products of iodination are conveniently separated from byproducts by simple treatment with anionic exchange resin Amberlite IRA 900 HCO3 - and are isolated with good purity after evaporation of the solvent. The reduced form of the hypervalent iodine oxidant, m-iodobenzoic acid, can be recovered in 91-95% yield from the Amberlite resin by treatment with aqueous hydrochloric acid followed by extraction with ethyl acetate.

Язык оригиналаАнглийский
Номер статьиM04210SS
Страницы (с-по)3681-3685
Число страниц5
ЖурналSynthesis
Номер выпуска21
DOI
СостояниеОпубликовано - 2010

Отпечаток

Ketones
Iodine
Oxidants
Acids
Iodobenzoates
Resins
Carbonyl compounds
Hydrochloric Acid
Hydrochloric acid
Byproducts
Evaporation
amberlite

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

Цитировать

M-iodosylbenzoic acid as a convenient recyclable hypervalent iodine oxidant for the synthesis of α-iodo ketones by oxidative iodination of ketones. / Yusubov, Mehman S.; Yusubova, Rosa Y.; Funk, Tatyana V.; Chi, Ki Whan; Kirschning, Andreas; Zhdankin, Viktor Vladimirovich.

В: Synthesis, № 21, M04210SS, 2010, стр. 3681-3685.

Результат исследований: Материалы для журналаСтатья

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abstract = "A convenient procedure for the preparation of -iodo ketones by oxidative iodination of ketones using iodine and m-iodosylbenzoic acid as a recyclable hypervalent iodine oxidant is reported. Various ketones and -dicarbonyl compounds can be iodinated by this reagent system under mild conditions affording the respective -iodo-substituted carbonyl compounds in excellent yields. The final products of iodination are conveniently separated from byproducts by simple treatment with anionic exchange resin Amberlite IRA 900 HCO3 - and are isolated with good purity after evaporation of the solvent. The reduced form of the hypervalent iodine oxidant, m-iodobenzoic acid, can be recovered in 91-95{\%} yield from the Amberlite resin by treatment with aqueous hydrochloric acid followed by extraction with ethyl acetate.",
keywords = "halogenation, hypervalent iodine, iodine, iodosylbenzene, ketones, m -iodosylbenzoic acid",
author = "Yusubov, {Mehman S.} and Yusubova, {Rosa Y.} and Funk, {Tatyana V.} and Chi, {Ki Whan} and Andreas Kirschning and Zhdankin, {Viktor Vladimirovich}",
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T1 - M-iodosylbenzoic acid as a convenient recyclable hypervalent iodine oxidant for the synthesis of α-iodo ketones by oxidative iodination of ketones

AU - Yusubov, Mehman S.

AU - Yusubova, Rosa Y.

AU - Funk, Tatyana V.

AU - Chi, Ki Whan

AU - Kirschning, Andreas

AU - Zhdankin, Viktor Vladimirovich

PY - 2010

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N2 - A convenient procedure for the preparation of -iodo ketones by oxidative iodination of ketones using iodine and m-iodosylbenzoic acid as a recyclable hypervalent iodine oxidant is reported. Various ketones and -dicarbonyl compounds can be iodinated by this reagent system under mild conditions affording the respective -iodo-substituted carbonyl compounds in excellent yields. The final products of iodination are conveniently separated from byproducts by simple treatment with anionic exchange resin Amberlite IRA 900 HCO3 - and are isolated with good purity after evaporation of the solvent. The reduced form of the hypervalent iodine oxidant, m-iodobenzoic acid, can be recovered in 91-95% yield from the Amberlite resin by treatment with aqueous hydrochloric acid followed by extraction with ethyl acetate.

AB - A convenient procedure for the preparation of -iodo ketones by oxidative iodination of ketones using iodine and m-iodosylbenzoic acid as a recyclable hypervalent iodine oxidant is reported. Various ketones and -dicarbonyl compounds can be iodinated by this reagent system under mild conditions affording the respective -iodo-substituted carbonyl compounds in excellent yields. The final products of iodination are conveniently separated from byproducts by simple treatment with anionic exchange resin Amberlite IRA 900 HCO3 - and are isolated with good purity after evaporation of the solvent. The reduced form of the hypervalent iodine oxidant, m-iodobenzoic acid, can be recovered in 91-95% yield from the Amberlite resin by treatment with aqueous hydrochloric acid followed by extraction with ethyl acetate.

KW - halogenation

KW - hypervalent iodine

KW - iodine

KW - iodosylbenzene

KW - ketones

KW - m -iodosylbenzoic acid

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