Preparation, structure, and oxidative reactivity of (dichloroiodo)pyridines

Recyclable hypervalent iodine reagents

Akira Yoshimura, Khiem C. Nguyen, Victor N. Nemykin, Viktor V. Zhdankin

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)40-49
Number of pages10
JournalArkivoc
Volume2018
Issue number2
DOIs
Publication statusPublished - 11 Oct 2017

Fingerprint

Pyridines
Iodine
Carbonyl compounds
Chlorination
X ray crystallography
Liquids
Alcohols
Oxidation
Acids
Temperature
propoxypyridine
pyridine

Keywords

  • (Dichloroiodo)arenes
  • Hypervalent iodine
  • Iodopyridine
  • Oxidation
  • Recyclable reagents

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Preparation, structure, and oxidative reactivity of (dichloroiodo)pyridines : Recyclable hypervalent iodine reagents. / Yoshimura, Akira; Nguyen, Khiem C.; Nemykin, Victor N.; Zhdankin, Viktor V.

In: Arkivoc, Vol. 2018, No. 2, 11.10.2017, p. 40-49.

Research output: Contribution to journalArticle

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