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 | |
| State | Published - Nov 1 2010 |
Keywords
- halogenation
- hypervalent iodine
- iodine
- iodosylbenzene
- ketones
- m -iodosylbenzoic acid