Details
| Original language | English |
|---|---|
| Article number | M04210SS |
| Pages (from-to) | 3681-3685 |
| Number of pages | 5 |
| Journal | Synthesis |
| Issue number | 21 |
| Publication status | Published - 20 Aug 2010 |
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
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Synthesis, No. 21, M04210SS, 20.08.2010, p. 3681-3685.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
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 - 2010/8/20
Y1 - 2010/8/20
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
UR - http://www.scopus.com/inward/record.url?scp=77958542072&partnerID=8YFLogxK
U2 - 10.1055/s-0030-1258223
DO - 10.1055/s-0030-1258223
M3 - Article
AN - SCOPUS:77958542072
SP - 3681
EP - 3685
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 21
M1 - M04210SS
ER -