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Separation and recycling of phosphane ligands from homogeneously catalyzed processes / von László Majoros. 2006
Inhalt
1 Introduction
2 General Part
2.1 Influence of the chirality on the behavior of the compounds
2.2 Enantiomerically pure compounds
2.3 Catalysis
2.3.1 Homogeneous vs. heterogenenous catalysis
2.4 Asymmetric reduction
2.4.1 Enantioselective hydrogenation
2.4.2 Mechanism of the asymmertric hydrogenation
2.4.3 Asymmetric homogeneous hydrogenation using metal-catalyst in industrial application
2.4.4 Chiral Cl-MeO-Biphep ligand
2.5 Palladium catalyzed C-N bond-forming process
2.5.1 General Buchwald-Hartwig amination reaction [61]
2.5.2 Proposed Mechanism of the amination reaction
2.5.3 Dave-Phos and X-Phos ligands applied in C-N formation
2.6 Biphasic systems for reuse and recycling of the catalyst complexes
2.6.1 Immobilization by aqueous catalysts
2.6.2 Immobilization by nonaqueous biphasic systems
2.6.3 Immobilization and fixation to supported organic and inorganic polymers or matrices
3 Results and Discussion
3.1 Aims and Scopes
3.2 Asymmetric hydrogenation with different conditions and solvents using Cl-MeO-Biphep and BINAP ligands
3.2.1 Comparison of the two biaryl type phosphine ligands 3 and 11
3.2.2 Use of different solvents for the reduction of 1
3.2.3 Applying IL as a medium for the enantioselective hydrogenation of 1
3.2.4 Investigation of σ-ability of Cl-MeO-Biphep (3)
3.2.5 Scale up reaction for asymmetric hydrogenation in the research laboratory of Lanxess FC
3.2.6 Further improvement of asymmetric hydrogenation for the industrial applications with the view of costs
3.3 Derivatization of Cl-MeO-Biphep ligand (3)
3.4 Optimization of the recycling procedure of Cl-MeO-Biphep ligand via oxide derivative 3a and its scale up
3.4.1 Designing a separation and recycling cycle to demonstrate the steps of the complete procedure
3.4.2 Optimization of the reduction step using the standard oxide 3a
3.4.3 Optimization of the recovery cycle
3.4.4 Modeling of the recycling procedure as an industrial process
3.5 Results of Buchwald-Hartwig amination and the recycling process applying Dave-Phos and X-Phos ligands
4 Summary and Outlook
4.1 Summary
4.2 Outlook
5 Experimental Part
5.1 General Technique
5.2 Characterisation and use of ligand 3 in asymmetric hydrogenation
5.3 Derivatization of ligand 3
5.4 Optimization of the recycling cycle for ligand 3
5.5 Amination reaction using Dave-Phos (7) and X-Phos (8) ligand
6 Spectra
7 Literature
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