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

Paper ID Volume ID Publish Year Pages File Format Full-Text
42769 45940 2009 6 PDF Available
Title
Quaternary ammonium salts ionic liquids for immobilization of chiral Ru-BINAP complexes in asymmetric hydrogenation of β-ketoesters
Abstract

Chiral catalytic complex (R)—[RuCl(binap)(p-cymene)]Cl was used in asymmetric hydrogenation of methyl acetoacetate to methyl-3-hydroxybutyrate in the mixed methanol-ionic liquid phase. Quaternary ammonium salts ionic liquids, namely n-alkyl-triethylammonium bis(trifluoromethane sulfonyl) imides (NR222Tf2N, R = 6, 7, 8, 10, 12, 14), were prepared and employed in this transformation. Enough evidence was provided that only a small amount of this type of IL in a conventional solvent was necessary to accommodate the catalytic complex and that the reaction could be carried out with very high enantioselectivity. Similarly it was proved that under optimized conditions the catalytic complex immobilized in this manner could be used repeatedly. A part of the work was focused on the role of the alkyl chain length in the NR222Tf2N ionic liquid which was found as very essential. Role of the reaction impurities with origin in the synthesis of the employed ILs was also investigated.

Graphical abstractQuatenary ammonium ionic liquids, namely n-alkyl-triethylammonium bis(trifluoromethane sulfonyl) imides (NR222Tf2N, R = 6,7,8,10,12,14), were used to accommodate the catalytic Ru-BINAP complex in the stereoselective hydrogenation of MAA. The role of the alkyl chain length in the NR222Tf2N ionic liquid was found essential.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Asymmetric hydrogenation; Stereoselectivity; Ionic liquids; Ru-BINAP; Quaternary ammonium salts
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Quaternary ammonium salts ionic liquids for immobilization of chiral Ru-BINAP complexes in asymmetric hydrogenation of β-ketoesters
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 366, Issue 1, 15 September 2009, Pages 160–165
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
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