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 Vladimirovich Zhdankin

Research output: Contribution to journalArticle

24 Citations (Scopus)

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
Pages (from-to)3812-3819
Number of pages8
JournalJournal of Organic Chemistry
Volume76
Issue number10
DOIs
Publication statusPublished - 20 May 2011

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Iodine
X rays
Oxidation
Sodium Hydroxide
Sulfides
Organic solvents
X ray diffraction analysis
Solubility
Alcohols
Single crystals
propoxypyridine
alkoxyl radical
dimethyldioxirane
acetonitrile
sulfuric acid
2-iodopyridine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Preparation, X-ray structure, and reactivity of 2-iodylpyridines : Recyclable hypervalent iodine(V) reagents. / Yoshimura, Akira; Banek, Christopher T.; Yusubov, Mekhman S.; Nemykin, Victor N.; Zhdankin, Viktor Vladimirovich.

In: Journal of Organic Chemistry, Vol. 76, No. 10, 20.05.2011, p. 3812-3819.

Research output: Contribution to journalArticle

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AB - 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.

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