Abstract
New pyridine-based hypervalent iodine reagents, (dichloroiodo)pyridines, were prepared by chlorination of 2-, 3-, or 4-iodopyridines with NaOCl-HCl at room temperature. Structures of 2-(dichloroiodo)pyridine and 2-(dichloroiodo)-3-propoxypyridine were established by X-ray crystallography. The new (dichloroiodo)pyridines can be used as efficient reagents for oxidation of alcohols to carbonyl compounds and also as chlorinating reagents. The reduced form of the reagents such as 2-iodo-3-propoxypyridine, can be recovered from the reaction mixture in good yields by an acid-base liquid-liquid biphasic protocol.
| Original language | English |
|---|---|
| Pages (from-to) | 40-49 |
| Number of pages | 10 |
| Journal | Arkivoc |
| Volume | 2018 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 11 Oct 2017 |
Keywords
- (Dichloroiodo)arenes
- Hypervalent iodine
- Iodopyridine
- Oxidation
- Recyclable reagents
ASJC Scopus subject areas
- Organic Chemistry
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Cite this
Yoshimura, A., Nguyen, K. C., Nemykin, V. N., & Zhdankin, V. V. (2017). Preparation, structure, and oxidative reactivity of (dichloroiodo)pyridines: Recyclable hypervalent iodine reagents. Arkivoc, 2018(2), 40-49. https://doi.org/10.24820/ark.5550190.p010.279