ChemInform Abstract: Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent: Leading to Galanthamine‐Type Amaryllidaceae Alkaloids.
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.Keywords:
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[reaction: see text] One-pot hypervalent iodine-mediated oxidations of arylsulfinamides to arylsulfonimidates is reported. Contrary to the case of alkylsulfinamides, use of iodosobenzene was not satisfactory. The reaction worked best with diacetoxyiodosobenzene (DIB) and a mild base (MgO). The influence of substituents on the iodine(III) reagent arene has been examined.
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Base (topology)
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Abstract The hypervalent iodine oxidant, consisting of m‐iodosylbenzoic acid and iodine, iodinates various enolizable ketones and β‐dicarbonyl compounds under mild conditions providing the corresponding α‐iodo‐substituted carbonyl compounds in good to excellent yields.
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Iodine compounds
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Iodine oxygen bonds of hypervalent 10-I-3 iodine(III) compounds with T-shaped geometry were investigated using analysis of the Cambridge Crystallographic Database and ab initio molecular orbital calculations.The statistical analysis of the I-O bond lengths revealed an average of 2.14 Å and a strong correlation between the two bond lengths.
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Abstract Non‐iodinated arenes can be easily and selectively converted into (diacetoxyiodo)arenes in a single step under mild conditions by using iodine triacetates as reagents. The oxidative step is decoupled from the synthesis of hypervalent iodine(III) reagents, which can now be prepared conveniently in a one‐pot synthesis for subsequent reactions without prior purification. The chemistry of iodine triacetates was also expanded to heteroatom ligand exchanges to form novel inorganic hypervalent iodine compounds.
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The fast access to simple (Z)-3-iodo acrylic acid derivatives which can be easily oxidized to the corresponding hypervalent iodine(III) reagents is described. They can be used for various reactions with superior or similar reactivity as conventional hypervalent iodine(III) reagents.
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Iodine compounds
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Hexafluoroisopropan-2-ol (HFIP) is an excellent solvent for promoting fluorinations with the hypervalent fluoroiodane reagent 1 and crucially, it removes the need for transition metals or TREAT-HF activators. The fluoroiodane reagent 1 was used in HFIP to monofluorinate 1,3-ketoesters and to fluorocyclise unsaturated carboxylic acids in excellent yields under mild reaction conditions.
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Potassium 4-iodylbenzenesulfonate (PIBS) is a thermally stable and water soluble hypervalent iodine oxidant particularly useful as a recyclable reagent for oxidative iodination of alkenes, alkynes and ketones. This reagent can be effectively recovered from the reaction mixture by treatment of the aqueous layer with Oxone at 60 °C followed by filtration of the precipitate. Keywords: Iodination, iodine, iodoketones, alkyl iodides, iodomethoxylation, hypervalent iodine.
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Surface Modification
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A novel imidazolium-based ionic liquid-supported hypervalent iodine reagent has been synthesized and employed for a 'catch and release' strategy with substituted acetophenones to generate various α-substituted acetophenones in good to excellent yields. The use of an ionic liquid-supported hypervalent iodine reagent avoids chromatographic separation for the purification of α-substituted acetophenones and thus makes the method greener.
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A convenient approach for the synthesis of β-cyanoepoxides is illustrated by iodine(III)-catalyzed epoxidation of electron-deficient β-cyanostyrenes, wherein the active catalytic iodine(III) species was generated in situ. The epoxidation of β-cyanostyrenes was performed using 10 mol% PhI as precatalyst in the presence of 2.0 equivalents Oxone as an oxidant and 2.4 equivalents of TFA as an additive at room temperature under ultrasonic radiations. The β-cyanoepoxides were isolated in good to excellent yields in a short reaction time.
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