Chapter
1.2.2 Sulfonic or Carboxylic Acid-Amine Bifunctional Catalyst
1.3 Bifunctional Catalysts Possessing Basic Organic Groups and Acid Sites Derived from Their Support Surface
1.3.1 Organic Base-Catalyzed Reactions Enhanced by SiO2
1.3.2 Amine-Catalyzed Reactions Enhanced by Acid Site on Silica-Alumina
1.3.3 Control of Acid-Base Interaction on Solid Surface
1.3.4 Cooperative Catalysis of Acid Site, Primary Amine, and Tertiary Amine
Chapter 2 Catalytic Reactions in or by Room-Temperature Ionic Liquids: Bridging the Gap between Homogeneous and Heterogeneous Catalysis
2.1 Introduction and Background
2.2 Catalysis with IL-Supported or Mediated Metal Nanoparticles
2.2.1 Preparation of MNPs in ILs
2.2.1.1 IL Itself as the Reducing Agent
2.2.1.2 Molecular Hydrogen as Reducing Agent
2.2.1.3 NaBH4 as the Reducing Agent
2.2.1.4 Other Reducing Agents
2.2.2 Characterization of IL-Supported or Mediated MNPs
2.2.2.3 Molecular Dynamics Simulations
2.2.3 Hydrogenation Reactions
2.2.4 IL-Supported Pd NPs
2.2.5 IL-Supported Pt and Ir NPs
2.2.6 IL-Supported Ru NPs
2.2.6.1 IL-Supported Rh NPs
2.2.7 C-C Coupling Reactions
2.2.7.2 Mizoroki-Heck Reaction
2.2.7.4 Sonogashira Reaction
2.3 Reactions Catalyzed by Solid-Supported IL: Heterogeneous Catalysis with Homogeneous Performance
2.3.1.1 Design, Preparation, and Properties of Supported IL-Phase Catalysis
2.3.2 Design, Preparation, and Properties of Silica Gel-Confined IL Catalysts
2.3.2.1 Design, Preparation, and Properties of Covalently Supported IL Catalysts
2.3.3 Catalytic Reaction with Supported IL Catalysts
2.3.3.1 Catalytic Hydrogenation
2.3.3.2 Selective Oxidation
2.3.3.3 Catalytic Carbonylation Reaction
2.3.3.4 Water-Gas Shift Reaction
2.3.3.5 Isomerization and Oligomerization
2.3.3.6 Alkylation and Esterification Reactions
2.3.3.7 Asymmetric Catalysis
Chapter 3 Heterogeneous Catalysis with Organic-Inorganic Hybrid Materials
3.1.1 Ordered Mesoporous Silica
3.1.2 Organic-Inorganic Hybrid Materials
3.1.3 Heterogeneous Catalysis
3.2 Organic-Inorganic Hybrid Materials
3.2.1 General Advantages of Organic-Inorganic Hybrid Materials
3.2.2 Grafting and Co-Condensation
3.2.2.2 Ionic Liquids (ILs)
3.2.3 Periodic Mesoporous Organosilicas (PMOs)
3.2.3.1 Synthesis of PMOs with Surfactants
3.2.3.4 Hybrid Periodic Mesoporous Organosilica (HPMO)
3.3 Catalysis of Organic-Inorganic Hybrid Materials
3.3.1 Catalytic Application of Organic-Functionalized Mesoporous Silica by Grafting and Co-Condensation Method
3.3.1.1 Knoevenagel Condensation
3.3.1.2 Aldol Condensation
3.3.1.3 Esterification of Alcohol
3.3.2 Catalytic Application of Periodic Mesoporous Organosilica
3.4 Summary and Conclusion
Chapter 4 Homogeneous Asymmetric Catalysis Using Immobilized Chiral Catalysts
4.2 Soluble Polymeric Supports and Catalyst Separation Methods
4.2.1 Types of Soluble Polymeric Supports
4.2.2 Immobilized Catalyst Separation Methods
4.3 Chiral Linear Polymeric Catalysts
4.4 Chiral Dendritic Catalysts
4.5 Helical Polymeric Catalysts
4.6 Conclusion and Prospects
Chapter 5 Endeavors to Bridge the Gap between Homo- and Heterogeneous Asymmetric Catalysis with Organometallics
5.2 Combinatorial Approach for Homogeneous Asymmetric Catalysis
5.2.1 The Principle of Combinatorial Approach to Chiral Catalyst Discovery
5.2.2 Ti(IV)-Catalyzed Enantioselective Reactions
5.2.2.1 Schiff Base/Ti(IV)-Catalyzed Asymmetric Hetero-Diels-Alder Reaction
5.2.2.2 BINOLate/Ti(IV)-Catalyzed Asymmetric Hetero-Diels-Alder Reaction
5.2.2.3 BINOLate/Ti-Catalyzed Asymmetric Carbonyl-Ene Reaction
5.2.2.4 BINOLate/Ti-Catalyzed Asymmetric Ring-Opening Aminolysis of Epoxides
5.2.3 Zn Complex-Catalyzed Enantioselective Reactions
5.2.3.1 Chiral Amino Alcohol/Zn/Racemic Amino Alcohol-Catalyzed Asymmetric Diethylzinc Addition to Aldehydes
5.2.3.2 BINOLate/Zn/Diimine-Catalyzed Asymmetric Diethylzinc Addition to Aldehydes
5.2.3.3 BINOLate/Zn/Diimine-Catalyzed Asymmetric Hetero-Diels-Alder Reaction
5.2.4 Ru Complex-Catalyzed Enantioselective Reactions
5.2.4.1 Achiral Monophosphine/Ru/Chiral Diamine-Catalyzed Asymmetric Hydrogenation of Ketones
5.2.4.2 Achiral Bisphosphine/Ru/Chiral Diamine-Catalyzed Asymmetric Hydrogenation of Ketones
5.3 Self-Supporting Approach for Heterogeneous Asymmetric Catalysis
5.3.1 The Principle of Design and Generation of Self-Supported Catalysts
5.3.2 Self-Supported BINOLate/Ti(IV)-Catalyzed Asymmetric Carbonyl-Ene Reaction
5.3.3 Self-Supported BINOLate/Ti(IV)-Catalyzed Asymmetric Sulfoxidation Reaction
5.3.4 Self-Supported BINOLate/La(III)-Catalyzed Asymmetric Epoxidation
5.3.5 Self-Supported BINOLate/Zn(II)-Catalyzed Asymmetric Epoxidation
5.3.6 Self-Supported Noyori-Type Ru(II)-Catalyzed Asymmetric Hydrogenation
5.3.7 Self-Supported MonoPhos/Rh(I)-Catalyzed Asymmetric Hydrogenation Reactions
5.3.7.1 Covalent Bonded Bridging Ligands for Self-Supported Catalysts
5.3.7.2 Hydrogen-Bonded Bridging Ligands for Self-Supported Catalysts
5.3.7.3 Metal-Coordinated Bridging Ligands for Self-Supported Catalysts
5.4 Conclusions and Outlook
Chapter 6 Catalysis in and on Water
6.2 Catalytic Reactions in and ``on'' Water
6.2.2.1 Achiral Hydrogenation
6.2.2.2 Asymmetric Hydrogenation
6.2.3.1 Diels-Alder Reaction
6.2.3.2 Friedel-Crafts Reaction
6.2.3.3 Suzuki-Miyaura Coupling
6.2.3.5 Alcohol Oxidation
Chapter 7 A Green Chemistry Strategy: Fluorous Catalysis
7.1 History of Fluorous Chemistry
7.2 Basics of Fluorous Chemistry
7.3 Fluorous Metallic Catalysis
7.3.1 Fluorous Palladacycle Catalysts
7.3.2 Fluorous Pincer Ligand-Based Catalysts
7.3.3 Fluorous Immobilized Nanoparticles Catalysts
7.3.4 Fluorous Palladium-NHC Complexes
7.3.5 Fluorous Phosphine-Based Palladium Catalyst
7.3.6 Fluorous Grubbs' Catalysts
7.3.7 Fluorous Silver Catalyst
7.3.8 Fluorous Wilkinson Catalyst
7.3.9 Miscellaneous Fluorous Catalysts
7.4 Fluorous Organocatalysis
7.4.1 Asymmetric Aldol Reaction
7.4.2 Morita-Baylis-Hillman Reaction
7.4.3 Asymmetric Michael Addition Reaction
7.4.4 Catalytic Oxidation Reaction
7.4.5 Catalytic Acetalization Reaction
7.4.6 Catalytic Condensation Reaction
7.4.7 Catalytic Asymmetric Fluorination Reaction
Chapter 8 Emulsion Catalysis: Interface between Homogeneous and Heterogeneous Catalysis
8.2 Emulsion Catalysis in the Oxidative Desulfurization
8.2.1 Emulsion Catalytic Oxidative Desulfurization Using H2O2 as Oxidant
8.2.2 Emulsion Catalytic Oxidative Desulfurization Using O2 as Oxidant
8.3 Emulsion Catalysis in Lewis Acid-Catalyzed Organic Reactions
8.4 Emulsion Catalysis in Reactions with Organocatalysts
8.5 Emulsion Formed with Polymer-Bounded Catalysts
8.5.1 Emulsion Catalysis Participated by Metal Nanoparticles Stabilized by Polymer
8.5.2 Polymer-Bounded Organometallic Catalysts in Emulsion Catalysis
8.6 Conclusion and Perspective
Chapter 9 Identification of Binding and Reactive Sites in Metal Cluster Catalysts: Homogeneous-Heterogeneous Bridges
9.2 Control of Binding in Metal-Carbonyl Clusters via Ligand Effects
9.3 Imaging of CO Binding on Noble Metal Clusters
9.4 Imaging of Open Sites in Metal Cluster Catalysis
9.5 Elucidating Kinetic Contributions of Open Sites: Kinetic Poisoning Experiments Using Organic Ligands
9.6 More Approaches to Poisoning Open Catalytic Active Sites to Obtain Structure Function Relationships
9.6.1 Using Atomic Layer Deposition of Al2O3 to Block Sites on Pd/Al2O3 Catalysts
9.6.2 Bromide Poisoning of Active Sites on Au/TiO2 Catalysts for CO Oxidation Reactions
9.6.3 Bromide Poisoning of Active Sites on Au/TiO2 Catalysts for Water-Gas Shift Reactions
9.7 Supported Molecular Iridium Clusters for Ethylene Hydrogenation
Chapter 10 Catalysis in Porous-Material-Based Nanoreactors: a Bridge between Homogeneous and Heterogeneous Catalysis
10.2 Preparation of Nanoreactors Based on Porous Materials
10.2.1 Mesoporous Silicas
10.2.2 Metal-Organic Frameworks (MOFs)
10.2.3 Surface Modification of Nanoreactors
10.2.3.1 Surface Modification of Mesoporous Silicas (MSs)
10.2.3.2 Surface Modification of MOFs
10.3 Assembly of the Molecular Catalysts in Nanoreactors
10.3.1 Incorporating Chiral Molecular Catalysts in Nanoreactors through Covalent-Bonding Methods
10.3.2 Immobilizing Chiral Molecular Catalysts in Nanoreactors through Noncovalent Bonding Methods
10.3.2.1 Introduction of Molecular Catalysts into Nanoreactors through Noncovalent Bonding Methods
10.3.2.2 Encapsulating Molecular Catalyst in Nanoreactors by Reducing the Pore Entrance Size
10.4 Catalytic Reactions in Nanoreactors
10.4.1 Pore Confinement Effect
10.4.2 Enhanced Cooperative Activation Effect in Nanoreactors
10.4.2.1 The Kinetic Resolution of Epoxides
10.4.2.2 Water Oxidation Reactions
10.4.2.3 Epoxide Hydration
10.4.3 Isolation Effect in Nanoreactors
10.4.3.1 Selectivity Control
10.4.3.2 Inhibiting Dimerization of Molecular Catalysts
10.4.4 Microenvironment Engineering of Nanoreactors
10.4.5 Influence of the Porous Structure on the Catalytic Performance of Nanoreactors
10.4.6 Catalytic Nanoreactor Engineering
10.5 Conclusions and Perspectives
Chapter 11 Heterogeneous Catalysis by Gold Clusters
11.2 Preparation of Gold Clusters
11.2.1 Chemical Reduction
11.2.1.1 Phosphorus Ligands
11.2.2 Physical Vapor Deposition
11.2.3 Electrical Reduction
11.3 Characterization of Gold Clusters
11.4 Catalysis by Gold Clusters
11.4.1 Selective Hydrogenation
11.4.2 Selective Oxidation
11.4.2.1 Oxygen Activation
11.5 Conclusions and Perspectives
Chapter 12 Asymmetric Phase-Transfer Catalysis in Organic Synthesis
12.2 Chiral Phase-Transfer Catalysts
12.2.1 Chiral Crown Ethers - Cation-Binding Phase-Transfer Catalysts
12.2.2 Chiral Cation Phase-Transfer Catalysts
12.2.2.1 Chiral Quaternary Ammonium Salts
12.2.2.2 Chiral Quaternary Phosphonium Salts
12.2.3 Chiral Anion Phase-Transfer Catalysts
12.3 Asymmetric Phase-Transfer Catalytic Reactions and Applications
12.3.1 Asymmetric Phase-Transfer Reactions of Glycine Imine Derivatives
12.3.1.1 Asymmetric Alkylations
12.3.1.2 Asymmetric Conjugate Additions
12.3.1.3 Asymmetric Aldol and Mannich Condensations
12.3.2 Asymmetric Phase-Transfer Reactions of 1,3-Dicarbonyl Derivatives
12.3.3 Asymmetric Phase-Transfer Reactions of Oxindoles
12.3.4 Asymmetric Phase-Transfer Reactions of Nitroalkanes
12.3.5 Asymmetric Phase-Transfer Cyclization Reactions
12.3.6 Asymmetric Phase-Transfer Fluorination and Trifluoromethylation Reactions
12.3.7 Asymmetric Phase-Transfer Cyanation Reactions
12.3.8 Other Asymmetric Phase-Transfer Reactions
Chapter 13 Catalysis in Supercritical Fluids
13.2 Features of Supercritical Fluids and Related Catalytic Reactions
13.2.1 Properties of Supercritical Fluids
13.2.2 Features of Reactions in Supercritical Fluids
13.3 Examples of the Reactions in SCFs
13.3.1 Hydrogenation of Organic Substances
13.3.2 Hydrogenation of CO2
13.3.3 Hydroformylation Reactions
13.3.6 CO2 Cycloaddition to Epoxide
13.4 Summary and Conclusions
Chapter 14 Hydroformylation of Olefins in Aqueous-Organic Biphasic Catalytic Systems
14.2 Water-Soluble Rhodium-Phosphine Complex Catalytic Systems
14.4 Hydroformylation of Lower Olefins
14.5 Hydroformylation of Higher Olefins
14.5.1 Supported Aqueous-Phase Catalysts
14.5.5 Thermoregulated Inverse Phase-Transfer Catalysts
14.6 Hydroformylation of Internal Olefins
14.7 Conclusion and Outlook
Chapter 15 Recent Progress in Enzyme Catalysis in Reverse Micelles
15.2 Enzyme Catalysis in Molecular Organic Solvent-Based Reverse Micelles
15.2.1 Effect of Interfacial Property of Reverse Micelles on Enzyme Catalysis
15.2.1.1 Effect of the Electrical Property of the Interface
15.2.1.2 Effect of the Size and Structure of Surfactant Head Group
15.2.2 Effect of Additives on Enzyme Catalysis in Reverse Micelles
15.2.2.1 Ionic Liquids as Additives
15.2.2.2 Nanomaterials as Additives
15.2.3 Relationship between the Conformation and the Activity of Enzymes in Reverse Micelles
15.2.4 Pseudophase Model and Enzyme-Catalyzed Reaction Kinetics in Reverse Micelles
15.3 Enzyme Catalysis in Ionic Liquid-Based Reverse Micelles
15.3.1 Microemulsification of Hydrophobic Ionic Liquids
15.3.2 Ionic Liquids as Surfactants
15.4 Application of Enzyme Catalysis in Reverse Micelles
15.4.1 Application in Biotransformation
15.4.2 Reverse Micelle-Based Gel and Its Application for Enzyme Immobilization
Chapter 16 The Molecular Kinetics of the Fischer-Tropsch Reaction
16.2 Basics of the Fischer-Tropsch Kinetics
16.2.1 Mechanistic Background of the Carbide-Based Mechanism
16.2.2 General Kinetics Considerations
16.2.2.1 Some Mathematical Expressions
16.3 Molecular Microkinetics Simulations
16.3.1 Analysis of Microkinetics Results
16.3.1.1 Monomer Formation Limited Kinetics Limit versus Chain Growth Model
16.3.1.2 Methane Formation versus Fischer-Tropsch Kinetics
16.4 The Lumped Kinetics Model
16.4.1 The Single Reaction Center Site Model
16.4.2 The Dual Reaction Center Site Model
16.6 Conclusion and Summary
Bridging Heterogeneous and Homogeneous Catalysis
：Concepts, Strategies, and Applications
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