Repetitive Application of a Fluorous Chiral BINAP–Ru Complex in the Asymmetric Hydrogenation of Olefins

Horn, Joachim; Bannwarth, Willi

doi:10.1002/ejoc.200601068

Cited by 23 publications

(4 citation statements)

References 36 publications

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“…Other researchers have also reported the importance of the pore size of silica in the asymmetric hydrogenation of olefins. 16 Because various types of mesoporous silicas have recently been synthesized, 17 mesoporous silica capable of promoting the cycloaddition of CO 2 to epoxides more efficiently may be found in future. The time course of the 1a-catalyzed formation of cyclic carbonate 9a is shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Highly active and robust organic–inorganic hybrid catalyst for the synthesis of cyclic carbonates from carbon dioxide and epoxides

2008

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A high-throughput combinatorial strategy enabled us to find a highly active organic-inorganic hybrid catalyst for the production of cyclic carbonates from CO 2 and epoxides. The best hybrid catalyst 1a was prepared by the coupling of 3-(triethoxysilyl)propyltriphenylphosphonium bromide and mesoporous silica, and the organic and inorganic moieties had a synergistic effect on catalytic activity. The pore size of silica was found to be important for catalysis; mesoporous silica with the mean pore size of 19 nm exhibited much better performance than silica with that of 6 nm. The solvent-free and metal-free reactions proceeded successfully under very mild conditions (1 MPa, 90 • C, 1 mol% loading of catalyst, 6 h), and the hybrid catalyst could be recycled ten times.

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Section: Resultsmentioning

confidence: 99%

Highly active and robust organic–inorganic hybrid catalyst for the synthesis of cyclic carbonates from carbon dioxide and epoxides

2008

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“…The perfluoroalkyl-tagged ( S )-BINAP 276 (Figure ) was tested for the ruthenium-catalyzed asymmetric hydrogenation of N -acetyl-α-phenylethenamine in methanol . It gave the hydrogenated product with 44% ee in 64% yield.…”

Section: Hydrogenation Reactionsmentioning

confidence: 99%

Use of Nonfunctionalized Enamides and Enecarbamates in Asymmetric Synthesis

2011

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“…Later, Bannwarth 208,209 prepared (S)-6,6 0 -substituted perfluorinated bis-trialkylsilyl BINAP derivatives, via lithiation of benzyloxymethyl (BOM) protected dibromo-binaphthyl derivative followed by coupling with the trialkylsilyl bromide (Fig. 55C).…”

Section: Fluorinated Derivativesmentioning

confidence: 99%

Synthesis of binaphthyl based phosphine and phosphite ligands

et al. 2013

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The development of large scale synthesis of enantiopure and thermally stable (R)- and (S)-BINOL molecules constitutes a key milestone in the field of asymmetric catalysis. Particularly, a great variety of chiral binaphthyl-based phosphorus compounds, herein represented by phosphite and phosphine classes, have earned considerable relevance due to their versatility as ligands in enantioselective metal-catalysed reactions, allowing the preparation of optically active products with the desired enantiopurity. This review highlights the most relevant concepts and accounts regarding general synthetic procedures for binaphthyl-based mono- and bidentate phosphites and phosphines. Furthermore, the search for environmentally benign chemical catalytic processes compelled us to also give special attention to the functionalisation of binaphthyl-based phosphorus ligands for use in alternative reaction media. When available, a critical selection of their applications in catalysis is briefly assessed.

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Repetitive Application of a Fluorous Chiral BINAP–Ru Complex in the Asymmetric Hydrogenation of Olefins

Abstract: A trisperfluoroalkylsilyl-modified (S)-BINAP ligand has been prepared and its pertinent Ru complex applied to the asymmetric hydrogenation of olefins. Efficient separation of the Ru catalyst by filtration and its reuse was achieved. Relative

Cited by 23 publications

References 36 publications

Highly active and robust organic–inorganic hybrid catalyst for the synthesis of cyclic carbonates from carbon dioxide and epoxides

Highly active and robust organic–inorganic hybrid catalyst for the synthesis of cyclic carbonates from carbon dioxide and epoxides

Use of Nonfunctionalized Enamides and Enecarbamates in Asymmetric Synthesis

Synthesis of binaphthyl based phosphine and phosphite ligands

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