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 journalArticlepeer-review

5 Scopus citations

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 (US)
Pages (from-to)40-49
Number of pages10
JournalArkivoc
Volume2018
Issue number2
DOIs
StatePublished - Oct 11 2017

Bibliographical note

Funding Information:
This work was supported by a research grant from the NSF (CHE-1262479) and Tomsk Polytechnic University (VIU-316/2017).

Publisher Copyright:
© 2018 ARKAT USA, Inc.

Copyright:
Copyright 2018 Elsevier B.V., All rights reserved.

Keywords

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

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