Preparation, X-ray structure, and reactivity of 2-iodylpyridines: Recyclable hypervalent iodine(V) reagents

Akira Yoshimura, Christopher T Banek, Mekhman S. Yusubov, Victor N. Nemykin, Viktor Zhdankin

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

2-Iodylpyridine and four examples of 3-alkoxy-2-iodylpyridines were prepared by oxidation of the respective 2-iodopyridines with 3,3-dimethyldioxirane. Structures of 2-iodylpyridine, 2-iodyl-3- isopropoxypyridine, and 2-iodyl-3-propoxypyridine were established by single-crystal X-ray diffraction analysis. 2-Iodyl-3-propoxypyridine has moderate solubility in organic solvents (e.g., 1.1 mg/mL in acetonitrile) and can be used as a recyclable reagent for oxidation of sulfides and alcohols. The reduced form of this reagent, 2-iodo-3-propoxypyridine, can be effectively separated from the reaction mixture by treatment with diluted sulfuric acid and recovered from the acidic aqueous solution by adding aqueous sodium hydroxide.

Original languageEnglish (US)
Pages (from-to)3812-3819
Number of pages8
JournalJournal of Organic Chemistry
Volume76
Issue number10
DOIs
StatePublished - May 20 2011

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