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 V. Zhdankin

doi:10.1055/s-0030-1258223

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 V. Zhdankin

Chemistry & Biochemistry

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

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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.

Original language	English (US)
Article number	M04210SS
Pages (from-to)	3681-3685
Number of pages	5
Journal	Synthesis
Issue number	21
DOIs	https://doi.org/10.1055/s-0030-1258223
State	Published - Nov 1 2010

Keywords

halogenation
hypervalent iodine
iodine
iodosylbenzene
ketones
m -iodosylbenzoic acid

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

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 V.}",

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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 V.

PY - 2010/11/1

Y1 - 2010/11/1

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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ER -

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

Abstract

Keywords

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