- Preparation, structure, and oxidative reactivity of (dichloroiodo)pyridines: Recyclable hypervalent iodine reagents
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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.
- Yoshimura, Akira,Nguyen, Khiem C.,Nemykin, Victor N.,Zhdankin, Viktor V.
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- Oxidative Dehomologation of Aldehydes with Oxygen as a Terminal Oxidant
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A mild, efficient protocol for oxidative cleavage of C-C bonds in aldehydes has been developed that employs alkali metal hydrides as reagents and oxygen from air as a terminal oxidant. The method is applicable to a broad substrate range.
- Shipilovskikh, Sergei A.,Rubtsov, Aleksandr E.,Malkov, Andrei V.
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supporting information
p. 6760 - 6762
(2017/12/26)
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- 2-Iodoxybenzoic acid organosulfonates: Preparation, X-ray structure and reactivity of new, powerful hypervalent iodine(v) oxidants
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New powerful hypervalent iodine(v) oxidants, tosylate and mesylate derivatives of 2-iodoxybenzoic acid (IBX), were prepared by the reaction of IBX with the corresponding sulfonic acids. Single crystal X-ray crystallography of the diacetate derivative of IBX-tosylate revealed an unusual heptacoordinated iodine geometry without any significant intermolecular secondary interactions.
- Yusubov, Mekhman S.,Svitich, Dmitrii Yu.,Yoshimura, Akira,Nemykin, Victor N.,Zhdankin, Viktor V.
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supporting information
p. 11269 - 11271
(2013/12/04)
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- Facile preparation and reactivity of bifunctional ionic liquid-supported hypervalent iodine reagent: A convenient recyclable reagent for catalytic oxidation
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Novel, efficient, and recyclable bifunctional catalysts bearing ionic liquid supported (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) and iodoarene moieties were developed and used for environmentally benign catalytic oxidation of alcohols. The reactions using peracetic acid as a green and practical co-oxidant afforded the corresponding carbonyl compounds in high yields under mild conditions and convenient work-up. Furthermore, these ionic liquid supported bifunctional catalysts could be simply recovered and reused.
- Zhu, Chenjie,Yoshimura, Akira,Wei, Yunyang,Nemykin, Victor N.,Zhdankin, Viktor V.
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supporting information; experimental part
p. 1438 - 1444
(2012/04/04)
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- Facile preparation and reactivity of polystyrene-supported (dichloroiodo)benzene: A convenient recyclable reagent for chlorination and oxidation
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A facile one-pot preparation of polystyrene-supported (dichloroiodo)benzene (loading of -ICl2 up to 1.35 mmol/g) from polystyrene, iodine, and bleach has been developed. This recyclable reagent is useful for efficient chlorination of organic substrates and selective oxidation of various alcohols to the corresponding carbonyl compounds in high yields under mild conditions. The final products are conveniently separated from the polymeric byproduct by simple filtration and isolated in good purity after evaporation of solvent.
- Chen, Jiang-Min,Zeng, Xiao-Mei,Middleton, Kyle,Zhdankin, Viktor V.
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supporting information; experimental part
p. 1952 - 1955
(2011/04/25)
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- Preparation, X-ray structure, and reactivity of 2-iodylpyridines: Recyclable hypervalent iodine(V) reagents
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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.
- Yoshimura, Akira,Banek, Christopher T.,Yusubov, Mekhman S.,Nemykin, Victor N.,Zhdankin, Viktor V.
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experimental part
p. 3812 - 3819
(2011/07/08)
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- Highly efficient RuCl3-catalyzed disproportionation of (diacetoxyiodo)benzene to iodylbenzene and iodobenzene; leading to the efficient oxidation of alcohols to carbonyl compounds
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(Diacetoxyiodo)benzene (DIB) selectively oxidizes primary and secondary alcohols to the respective carbonyl compounds in the presence of RuCl3 (0.8-1.0 mol %) at room temperature in aqueous acetonitrile. This reaction proceeds via an initial instantaneous Ru-catalyzed disproportionation of DIB to iodobenzene and iodylbenzene with the latter acting as the actual stoichiometric oxidant toward alcohols.
- Yusubov, Mekhman S.,Chi, Ki-Whan,Park, Joo Yeon,Karimov, Rashad,Zhdankin, Viktor V.
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p. 6305 - 6308
(2007/10/03)
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- In situ alcohol oxidation-protection reactions
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The one-pot conversion of primary and secondary alcohols into phenylhydrazones and 2,4-dintrophenylhydrazones is reported using chromium trioxide supported on silica gel and phenylhydrazines or 2,4- dintrophenylhydrazines under solvent-free conditions. This oxidation arylhydrazone formation reaction has been applied to a range of aliphatic and benzylic alcohols. Copyright Taylor & Francis, Inc.
- Kiasat,Kazemi,Nourbakhsh
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p. 1555 - 1558
(2007/10/03)
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- A Novel Cleavage of Five-Membered Cyclic Acetals Using Sodium Hydrogen Telluride
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Under mild conditions, a variety of 1,3-dioxolanes are easily cleaved in high yields by treatment with sodium hydrogen telluride in ethanol.
- Lue, Ping,Fan, Wei-Qiang,Zhou, Xun-Jun
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p. 692 - 693
(2007/10/02)
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