Synthesis of 2,3-unsaturated glycopyranosides by Ferrier rearrangement in FeCl3 based ionic liquid

Tilve, Rutuja D.; Alexander, Matt; Khandekar, Amit C.; Samant, Sriniwas D.; Kanetkar, V. R.

doi:10.1016/j.molcata.2003.11.044

Cited by 65 publications

(26 citation statements)

References 20 publications

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“…In general, iron-containing ionic liquids have traditionally been applied to organic synthesis reactions such as hydroxymethylation, [2] alkylation, [3] sulfonylation, [4] synthesis of glycopyranosides, [5] and synthesis of diphenylmethane (DPM). [6] Meanwhile, these ionic liquids have also been applied in extractive desulfurization.…”

Section: Introductionmentioning

confidence: 99%

Oxidative Desulfurization of Fuels Catalyzed by Fenton‐Like Ionic Liquids at Room Temperature

Jiang

Zhu

et al. 2011

ChemSusChem

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Oxidation of the sulfur-containing compounds benzothiophene (BT), dibenzothiophene (DBT), and 4,6-dimethyldibenzothiophene (4,6-DMDBT) has been studied in a desulfurization system composed of model oil, hydrogen peroxide, and different types of ionic liquids [(C(8)H(17))(3)CH(3)N]Cl/FeCl(3), [(C(8)H(17))(3)CH(3)N]Cl/CuCl(2), [(C(8)H(17))(3)CH(3)N]Cl/ZnCl(2), [(C(8)H(17))(3)CH(3)N]Cl/SnCl(2), [(C(4)H(9))(3)CH(3)N]Cl/FeCl(3), [C(10)H(21)(CH(3))(3)N]Cl/FeCl(3), [(C(10)H(21))(2)(CH(3))(2)N]Cl/FeCl(3). Deep desulfurization is achieved in the Fenton-like ionic liquid [(C(8)H(17))(3)CH(3)N]Cl/FeCl(3) at 25 °C for 1 h. The desulfurization of DBT reaches 97.9%, in consuming very low amount of [(C(8)H(17))(3)CH(3)N]Cl/FeCl(3) (only 0.702 mmol). The reaction conditions, for example, the amount of [(C(8)H(17))(3)CH(3)N]Cl/FeCl(3) or H(2)O(2), the temperature, and the molar ratio of FeCl(3) to [(C(8)H(17))(3)CH(3)N]Cl, are investigated for this system. The oxidation reactivity of the different sulfur-containing compounds is found to decrease in the order of DBT>BT>4,6-DMDBT. The desulfurization system can be recycled six times without significant decrease in activity. The sulfur level of FCC gasoline could be reduced from 360 ppm to 110 ppm.

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Section: Introductionmentioning

confidence: 99%

Oxidative Desulfurization of Fuels Catalyzed by Fenton‐Like Ionic Liquids at Room Temperature

Jiang

Zhu

et al. 2011

ChemSusChem

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“…9 Glycosides have been also synthesized via Ferrier rearrangement starting from the corresponding unsaturated glycosides with alcohols in presence of InCl 3 , 10 Bi(OTf) 3 /SiO 2 -Bi(OTf) 3 11 and other acid catalysts. 12 In an environmentally benign chemistry on carbohydrates, i.e., green carbohydrate chemistry requires for clean, efficient and selective processes have increased the demand for such metal-based reaction promoters, especially in catalytic amounts. However, many catalysts are derived from heavy or rare metals and their toxicity and prohibitive prices constitute severe drawbacks for largescale applications.…”

Section: Introductionmentioning

confidence: 99%

“…15 In addition, iron chloride was successfully employed for the Ferrier rearrangement. 16 Whilst there are several published procedures [4][5][6][7][8][9][10][11][12] for the glycosylation reactions, many of these methods require the use of expensive reagents and have limitations in terms of yields, stereoselectivities, reaction temperature, the catalyst/reagents used and their quantitative amounts. Therefore, our aim was to find a method that utilized mild, relatively cheap reagents and flexible enough to allow the synthesis of glycosides.…”

Section: Introductionmentioning

confidence: 99%

Iron(III) chloride catalyzed glycosylation of peracylated sugars with allyl/alkynyl alcohols

Narayanaperumal¹,

Silva²,

Monteiro³

et al. 2012

J. Braz. Chem. Soc.

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Neste trabalho, o emprego de cloreto férrico como um eficiente catalisador em reações de glicosilação de açúcares na presença de álcoois alílicos e propargílicos é descrito. Os glicosídios correspondentes foram obtidos com rendimentos de moderados a bons. Este novo procedimento apresenta maior seletividade quando comparado a métodos clássicos encontrados na literatura. As principais características desse método simples incluem condições de reação não perigosas, quantidade de catalisador baixa, bom rendimento e seletividade anomérico elevada.In this work, the use of ferric chloride as an efficient catalyst in glycosylation reactions of sugars in the presence of allyl and alkynyl alcohols is described. The corresponding glycosides were obtained with moderate to good yields. This new procedure presented greater selectivity when compared to classic methods found in the literature. Principal features of this simple method include non-hazardous reaction conditions, low-catalyst loading, good yields and high anomeric selectivity.

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“…Tilve et al [12] studied the successful role of [bmim]Cl-FeCl 3 system as a solvent and a catalyst in the stereocontrolled glycosidation of 3,4,6-tri-O-acetyl-D-glucal with different alcohols. Sun et al [13] demonstrated the use of [bmim]ClFeCl 3 system for the alkylation of deuterated benzene with ethylene.…”

Section: Introductionmentioning

confidence: 99%

An iron(III)-containing ionic liquid: characterization, magnetic property and electrocatalysis

Wang

Zhang

Zhuang

et al. 2011

Transition Met Chem

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The present work reports on the synthesis, characterization and performance of a new iron(III)-containing ionic liquid [(C 4 H 9 ) 2 -bim][FeCl 4 ] (Fe-IL, bim = benzimidazolium) as an electrocatalyst for nitrite and bromate reduction. The melting point of Fe-IL is 70°C. Thermal behavior of the Fe-IL was studied by differential scanning calorimetry and thermalgravimetry. The value of magnetic moment and its temperature dependence were measured. A conductive carbon paste electrode (Fe-IL/CPE) comprised of Fe-IL and carbon powder was fabricated by the direct mixing method. The Fe-IL has double functions-a binder and an electrocatalyst. The electrochemical behavior and electrocatalysis of Fe-IL/CPE have been studied by cyclic voltammetry. The Fe-IL/CPE shows excellent electrocatalytic activities toward nitrite and bromate reduction. The detection limit and the sensitivity are 0.01 lM and 100.58 lA lM -1 for nitrite, and 0.01 lM and 83.11 lA lM -1 for bromate detection, respectively. This work demonstrates that the Fe-IL may become a new kind of functional material in constructing chemicals and biosensors.

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Synthesis of 2,3-unsaturated glycopyranosides by Ferrier rearrangement in FeCl3 based ionic liquid

Cited by 65 publications

References 20 publications

Oxidative Desulfurization of Fuels Catalyzed by Fenton‐Like Ionic Liquids at Room Temperature

Oxidative Desulfurization of Fuels Catalyzed by Fenton‐Like Ionic Liquids at Room Temperature

Iron(III) chloride catalyzed glycosylation of peracylated sugars with allyl/alkynyl alcohols

An iron(III)-containing ionic liquid: characterization, magnetic property and electrocatalysis

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