TY - JOUR
T1 - Preparation, X-ray structure, and reactivity of 2-iodylpyridines
T2 - Recyclable hypervalent iodine(V) reagents
AU - Yoshimura, Akira
AU - Banek, Christopher T
AU - Yusubov, Mekhman S.
AU - Nemykin, Victor N.
AU - Zhdankin, Viktor
PY - 2011/5/20
Y1 - 2011/5/20
N2 - 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.
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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U2 - 10.1021/jo200163m
DO - 10.1021/jo200163m
M3 - Article
C2 - 21462949
AN - SCOPUS:79956081248
SN - 0022-3263
VL - 76
SP - 3812
EP - 3819
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 10
ER -