Cycloaddition of CO2 and epoxides catalyzed by imidazolium bromides under mild conditions: influence of the cation on catalyst activity

Anthofer, Michael H.; Wilhelm, Michael E.; Cokoja, Mirza; Markovits, Iulius I. E.; Pöthig, Alexander; Mink, J.; Herrmann, Wolfgang A.; Kühn, Fritz E.

doi:10.1039/c3cy01024d

Cited by 94 publications

(73 citation statements)

References 61 publications

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“…The imidazolium bromide 35,[37][38][39][40][41][42][43][44][45][46] and -perrhenate salts 29 were synthesised according to literature procedures. 1,2-Dimethylimidazole was purchased from Acros Organics.…”

Section: General Remarksmentioning

confidence: 99%

Influence of substituents on cation–anion contacts in imidazolium perrhenates

et al. 2015

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A series of imidazolium perrhenates with different substituents at the imidazolium ring were synthesised and characterised, including single crystal X-ray diffraction. The effect of the substitution pattern on the state of aggregation of the compounds, the charge delocalisation and the ion pairing interaction via hydrogen bonds was studied. Particularly the substitution at the C2 position of the imidazolium ring was shown to be crucial to fine-tune the ion contacts. Fluorinated substituents appear to exhibit enhanced interionic interactions. The ability to tune the degree of contacts of the perrhenate anion allows for adjusting the nucleophilicity of this anion.

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Section: General Remarksmentioning

confidence: 99%

Influence of substituents on cation–anion contacts in imidazolium perrhenates

et al. 2015

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“…Additionally, cyclic carbonates have found wide applications as polar aprotic solvents, electrolytes for lithium-ion batteries, and as intermediates in the manufacture of fine chemicals [4][5][6]. Nevertheless, CO2 is an unreactive molecule and high energy barrier of the noncatalyzed cycloaddition associated with CO2 is necessary for the reaction to occur spontaneously [7,8]. So far, a plethora of catalytic systems for producing cyclic carbonates has been successfully developed in order to reduce the activation energy of the cycloaddition reaction, including metal oxides [9,10], alkali metal salts [11,12], metal-salen complexes [13,14], metal-organic framework (MOF) [15,16], microporous polymer [17], graphitic carbon nitride [18,19] and ionic liquids [20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Cycloaddition of CO 2 and epoxides catalyzed by dicationic ionic liquids mediated metal halide: Influence of the dication on catalytic activity

Liu

Liang

et al. 2015

Journal of Molecular Catalysis A: Chemical

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“…[2][3][4][5] One of the most studied reactions involving the use of CO 2 is represented by its fixation onto epoxides to produce cyclic carbonates and/or polycarbonates. [20][21][22] It is worth to be mentioned that, as highlighted by Sakakura, 3 a temperature of 150 °C does not represent necessarily a drawback in industrial applications. 2, 6-10 Among the possible active species able to catalyze the synthesis of cyclic carbonates, 6 imidazolium ionic liquids have shown excellent performances acting as catalysts or co-catalysts, for the latter usually in combination with organometallic complexes with Lewis acid properties.…”

Section: Introductionmentioning

confidence: 99%

A polyhedral oligomeric silsesquioxane-based catalyst for the efficient synthesis of cyclic carbonates

Bivona

Fichera

Fusaro

et al. 2015

Catal. Sci. Technol.

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Polyhedral oligomeric silsesquioxane functionalized with imidazolium chloride peripheries ĲPOSS-Imi) was\ud successfully synthesized through a novel synthesis protocol. The solid was extensively characterized via 1H\ud NMR, 13C NMR and IR spectroscopy as well as combustion chemical analysis, mass spectrometry and transmission electron microscopy. Moreover, an in-depth investigation through 29Si NMR was performed.\ud POSS-Imi was used for the first time as a catalyst for the conversion of CO2 and epoxides into cyclic carbonates with excellent results in terms of both yield and selectivity. The catalyst displayed improved catalytic performance with respect to unsupported 1-butyl-3-methylimidazolium chloride. The enhanced activity was ascribed to the proximity effect generated by the increased local concentration of imidazolium\ud species surrounding the inorganic silsesquioxane core

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Cycloaddition of CO2 and epoxides catalyzed by imidazolium bromides under mild conditions: influence of the cation on catalyst activity

Cited by 94 publications

References 61 publications

Influence of substituents on cation–anion contacts in imidazolium perrhenates

Influence of substituents on cation–anion contacts in imidazolium perrhenates

Cycloaddition of CO 2 and epoxides catalyzed by dicationic ionic liquids mediated metal halide: Influence of the dication on catalytic activity

A polyhedral oligomeric silsesquioxane-based catalyst for the efficient synthesis of cyclic carbonates

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