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

Research output: Contribution to journalArticle

21 Citations (Scopus)

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.

Original languageEnglish
Article numberM04210SS
Pages (from-to)3681-3685
Number of pages5
JournalSynthesis
Issue number21
DOIs
Publication statusPublished - 2010

Fingerprint

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

Keywords

  • halogenation
  • hypervalent iodine
  • iodine
  • iodosylbenzene
  • ketones
  • m -iodosylbenzoic acid

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

Cite this

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.

In: Synthesis, No. 21, M04210SS, 2010, p. 3681-3685.

Research output: Contribution to journalArticle

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AU - Funk, Tatyana V.

AU - Chi, Ki Whan

AU - Kirschning, Andreas

AU - Zhdankin, Viktor Vladimirovich

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