M-iodosylbenzoic acid as a convenient recyclable hypervalent iodine oxidant for the synthesis of α-iodo ketones by oxidative iodination of ketones
- authored by
- Mehman S. Yusubov, Rosa Y. Yusubova, Tatyana V. Funk, Ki Whan Chi, Andreas Kirschning, Viktor V. Zhdankin
- 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.
- Organisation(s)
-
Institute of Organic Chemistry
- External Organisation(s)
-
Siberian State Medical University
University of Ulsan
University of Minnesota
- Type
- Article
- Journal
- Synthesis
- Pages
- 3681-3685
- No. of pages
- 5
- ISSN
- 0039-7881
- Publication date
- 20.08.2010
- Publication status
- Published
- Peer reviewed
- Yes
- ASJC Scopus subject areas
- Catalysis, Organic Chemistry
- Electronic version(s)
-
https://doi.org/10.1055/s-0030-1258223 (Access:
Unknown)
