Evaluating Lewis acid catalyzed hydroalkylation of alkenes in neat and in ionic liquids

Lanman, Heather E.; Nguyen, Rene‐Viet; Yao, Xiaoquan; Chan, T. H.; Li, Chao‐Jun

doi:10.1016/j.molcata.2007.03.059

Cited by 15 publications

(8 citation statements)

References 13 publications

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“…Eliminating the necessity of hazardous chlorinated solvents for this transformation, the Li group found that the ionic liquid, 1-butyl-3-methylimidazolium triflate, with 10 mol % SnBr 4 could provide alkylation of 1,3-diketones with alkenes (Scheme ). While investigating neat reaction conditions, 10 mol % Cu(OTf) 2 was also found to be effective. In 2008, the efficiency and the scope of the Cu(OTf) 2 -catalyzed alkylation were improved by Yu and co-workers .…”

Section: Alkylation Via Activation Of Olefinsmentioning

confidence: 85%

Transition-Metal-Catalyzed C–H Alkylation Using Alkenes

et al. 2017

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Alkylation reactions represent an important organic transformation to form C-C bonds. In addition to conventional approaches with alkyl halides or sulfonates as alkylating agents, the use of unactivated olefins for alkylations has become attractive from both cost and sustainability viewpoints. This Review summarizes transition-metal-catalyzed alkylations of various carbon-hydrogen bonds (addition of C-H bonds across olefins) using regular olefins or 1,3-dienes up to May 2016. According to the mode of activation, the Review is divided into two sections: alkylation via C-H activation and alkylation via olefin activation.

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Section: Alkylation Via Activation Of Olefinsmentioning

confidence: 85%

Transition-Metal-Catalyzed C–H Alkylation Using Alkenes

et al. 2017

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“…Bioenzymes are generally expensive for commercial use and difficult to recycle without activity loss. As an alternative, Brönsted acidic ionic liquid (IL) is becoming a popular choice of both solvent and catalyst for the Fischer esterifications and the other acid-catalyzed reactions [6][7][8][9]. This is because the Brönsted acidic ionic liquids have many unique properties including tunable acidity from different acid functional groups, low melting point, negligible vapor pressure, good solubility for most organic and inorganic compounds, and high thermal stability.…”

Section: Introductionmentioning

confidence: 99%

Reactivity of Brönsted acid ionic liquids as dual solvent and catalyst for Fischer esterifications

Wei

Xing

et al. 2009

Korean J. Chem. Eng.

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Several water-stable ionic liquids with different acidity and affinity were synthesized and applied as both solvents and acid catalysts for Fischer esterification of ethanol reacting with four aliphatic carboxylic acids (acetic acid, n-hexanoic acid, lauric acid, and stearic acid). Among the studied ionic liquids, [(n-bu-SO 3 H) MIM][HSO 4 ] (3-butyl-1-(butyl-4-sulfonyl) imidazolium sulfate) and [(n-bu-SO 3 H) MIM][p-TSO] (3-butyl-1-(butyl-4-sulfonyl) imidazolium toluenesulfonate) show higher reactivity for the production of ethyl esters. The catalytic activities of these ionic liquids are strongly dependent on the acidity of their anions and cations, as well as their hydrophilicity and affinity with the reactants. Water refluxing through the condenser may be another important reason for obtaining high conversion of esterification, indicating a water-sequester process is still needed in order to obtain a higher yield of ester in the ionic liquid catalyzed esterification system. Kinetics studies show the conversions of the acids increase with reaction temperature and time, and reach equilibrium within about two hours. The apparent activation energies are 39.1±2.0, 49.7± 2.5, 51.4±2.5 and 59.3±3.0 kJ·mol −1 for the formation of ethyl acetate, ethyl n-hexanoate, ethyl laurate and ethyl stearate, respectively.

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“…Bio-enzymes are expensive and difficult to recycle without activity loss. As an alternative, acidic ionic liquids, due to their unique properties such as tunable acidity by modifying with different acid functional groups, low melting point, negligible vapor pressure, good solubility for most organic and inorganic compounds and high thermal stability, is becoming a new kind of catalysts for most acid-catalyzed reactions [6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Study on the alcoholysis of isoflavone catalyzed by ionic liquids

Wei

Huang

Deng

et al. 2008

React Kinet Catal Lett

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Alcoholysis of soybean isoflavone glucosides by butanol catalyzed by acidic ionic liquids was studied. The effects of the ionic liquid catalyst type, catalyst concentration, reaction time and reaction temperature on glycoside conversions, and aglycons yields were investigated. The optimum reaction conditions are found to be as follows: 0.036 g mL -1 of ionic liquid [BIM]HSO 4 as catalyst, reaction temperature at 104±1ºC, reaction time of 100 min. Under these optimum reaction conditions near complete conversions of the three kinds of glycosides (daidzin, glycitin and genistin) are obtained. Furthermore, the kinetics parameters for the alcoholysis were estimated. The activation energies of alcoholysis for the three kinds of isoflavone glucosides are 124 kJ mol -1 , 67 kJ mol -1 and 115 kJ mol -1 , respectively.

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Evaluating Lewis acid catalyzed hydroalkylation of alkenes in neat and in ionic liquids

Cited by 15 publications

References 13 publications

Transition-Metal-Catalyzed C–H Alkylation Using Alkenes

Transition-Metal-Catalyzed C–H Alkylation Using Alkenes

Reactivity of Brönsted acid ionic liquids as dual solvent and catalyst for Fischer esterifications

Study on the alcoholysis of isoflavone catalyzed by ionic liquids

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