Quaternary ammonium salts ionic liquids for immobilization of chiral Ru-BINAP complexes in asymmetric hydrogenation of β-ketoesters

Floris, Tomas; Klusoň, Petr; Bartek, Lukas; Pelantová, Helena

doi:10.1016/j.apcata.2009.07.002

Cited by 44 publications

(23 citation statements)

References 50 publications

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“…Various organic reactions are successfully carried out in ionic liquids. Additionally, they are used as reaction media in reactions with transition metals such as oxidation [4,5], hydrogenation [6,7], hydroformylation [8,9], oligomerization [10,11], and so on [12,13]. Chauvin 2 ]PF 6 (nbd = norbornadiene) complex and reported a higher activity than that in acetone media [14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Catalytic Hydrogenation Activity of New N-Acyl-Benzotriazole Rh(I) and Ru(III) Complexes in [bmim][BF4]

Ünver

Yılmaz

2016

Catalysts

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Abstract:The hydrogenation activity of new N-acyl-benzotriazole Rh(I) and Ru(III) complexes in ionic liquid media is reported in this study. Both complexes were completely soluble in 1-butyl-3-methylimidazolium tetrafluoroborate, [bmim][BF 4 ], and they were able to catalyze the hydrogenation of styrene and 1-octene. While ethylbenzene conversion in styrene hydrogenation reached 84% when the Ru complex was used, 100% conversion was obtained with the Rh complex at 393 K in 6 h. Additionally, total conversion in 1-octene hydrogenation reached 100% with the Rh complex in [bmim] [BF 4 ] media. The hydrogenation of styrene and 1-octene in dimethyl sulfoxide (DMSO) and toluene was also studied to compare the solvent effect on catalytic system. The effect of some catalytic parameters such as temperature, H 2 (g) pressure, and catalyst amount on the conversion was examined, and it was found that the conversion increased parallel to the increasing temperature and H 2 pressure. The recyclability of catalysts was also investigated, and it was revealed that the Rh complex in particular maintained the activity for at least 10 cycles.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Catalytic Hydrogenation Activity of New N-Acyl-Benzotriazole Rh(I) and Ru(III) Complexes in [bmim][BF4]

Ünver

Yılmaz

2016

Catalysts

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“…This paper is a continuation of our recent works focused on the role of the alkyl chain length in the alkylammonium salts ILs on the progress of MAA hydrogenation and on the overall design of the asymmetric hydrogenation experiment [15,34,35]. We believe that from the general point of view the strategy described here might be useful for a practical design of an effective asymmetric synthesis via the hydrogenation reaction with a homogeneous chiral Ru-BINAP complex.…”

Section: Introductionmentioning

confidence: 87%

“…The preliminary experiments pointed out the very essential role of organic halides positively influencing [35] the TOF as well as the (enantio)selectivity. The effect of cation's structure of chlorides or bromides on the reaction rate has been studied in every detail and this subject will be covered in our next communication.…”

Section: Tuning the Reaction Systemmentioning

confidence: 99%

Notes on the Asymmetric Hydrogenation of Methyl Acetoacetate in Neoteric Solvents

Floris

Klusoň

Muldoon³

2009

Catal Lett

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Asymmetric hydrogenation of methyl acetoacetate to methyl (R)-3-hydroxybutyrate by [(R)-RuCl(binap)(p-cymen)]Cl has been studied in methanol-ionic liquid and methanol-dense CO 2 solvent systems. The ionic pairs triethylhexylammonium and 1-methylimidazolium with bis(trifluoromethane sulfonyl) imide and hexafluorophosphates were used. The role of ionic pairs on the kinetic parameters and (enantio)selectivity has been demonstrated. Although the CO 2 expanded methanol system suffered from a reduction in both reaction rate and product selectivity, this changed in the presence of water. The high selectivity of the optimized methanol-CO 2 -water-halide system was designed as a consequence of observed additive effects.

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“…Afterwards, methyl acetoacetate (Aldrich, MAA, 2 g in 10 ml methanol) was introduced into the reactor. More details are given elsewhere [21,22]. Reaction conversions and enantioselectivities (ee) were determined with help of GC using a chiral column MN Hydrodex-b-3P.…”

Section: Methodsmentioning

confidence: 99%

“…This paper is the continuation of our recent work on the immobilization of Ru-BINAP and utilization of ionic liquids not only as the reaction phase in stereoselective reactions with this catalyst [21,22].…”

Section: Introductionmentioning

confidence: 97%

Stereoselective hydrogenation of methyl acetoacetate over structurally different chiral ruthenium complexes

Floris

Klusoň

Slater

2010

Reac Kinet Mech Cat

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Structurally different chiral ruthenium complexes were used in the asymmetric hydrogenation of methyl acetoacetate to methyl (R)-3-hydroxybutanoate. The naphthalene and dioxazole biphosphine structure variations revealed a strong effect on the reaction rate and the parameter of enantioselectivity. The highest optical yields were achieved with catalysts bearing two metal centers and comprising the quaternary ammonium ionic character.

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Quaternary ammonium salts ionic liquids for immobilization of chiral Ru-BINAP complexes in asymmetric hydrogenation of β-ketoesters

Cited by 44 publications

References 50 publications

Synthesis, Characterization, and Catalytic Hydrogenation Activity of New N-Acyl-Benzotriazole Rh(I) and Ru(III) Complexes in [bmim][BF4]

Synthesis, Characterization, and Catalytic Hydrogenation Activity of New N-Acyl-Benzotriazole Rh(I) and Ru(III) Complexes in [bmim][BF4]

Notes on the Asymmetric Hydrogenation of Methyl Acetoacetate in Neoteric Solvents

Stereoselective hydrogenation of methyl acetoacetate over structurally different chiral ruthenium complexes

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