Note: Intro -- Aqueous-Phase Organometallic Catalysis -- Preface to the Second Edition -- Preface to the First Edition -- Contents -- Contributors -- 1 Introduction -- 1 Introduction -- 2 Basic Aqueous Chemistry -- 2.1 Organic Chemistry in Water -- 2.1.1 Introduction -- 2.1.2 Origin of the Reactivity in Water -- 2.1.3 Pericyclic Reactions -- 2.1.3.1 Diels - Alder Reactions -- 2.1.3.2 Hetero Diels - Alder Reactions -- 2.1.3.3 Other Cycloadditions -- 2.1.3.4 Claisen Rearrangements -- 2.1.4 Carbonyl Additions -- 2.1.4.1 Aldol-type Reactions -- 2.1.4.2 Michael-type Reactions -- 2.1.4.3 Allylation Reactions -- 2.1.5 Oxido-reductions -- 2.1.5.1 Oxidations -- 2.1.5.2 Reductions -- 2.1.6 Radical Reactions -- 2.1.7 Outlook -- 2.2 Organometallic Chemistry in Water -- 2.2.1 Introduction -- 2.2.2 Water as a Solvent and Ligand -- 2.2.3 Organometallic Reactions of Water -- 2.2.4 Catalytic Reactions with Water -- 2.2.4.1 Water-gas Shift Reaction -- 2.2.4.2 Wacker- Hoechst Acetaldehyde Process -- 2.2.4.3 Olefin Hydration -- 2.2.4.4 Hydrodimerization -- 2.2.5 Water-soluble Metal Complexes -- 2.2.6 Perspectives -- 2.3 Characterization of Organometallic Compounds in Water -- 2.3.1 Introduction -- 2.3.2 General Survey -- 2.3.3 Effect of High Hydrostatic Pressure on Aqueous Organometallic Systems -- 2.3.4 Aqueous Organometallics with Pressurized Gases -- 2.3.5 Concluding Remarks -- 3 Catalysts for an Aqueous Catalysis -- 3.1 Variation of Central Atoms -- 3.1.1 Transition Metals -- 3.1.1.1 Introduction -- 3.1.1.2 Water-soluble Catalysts by Virtue of Water-soluble Ligands -- 3.1.1.3 Water-soluble Catalysts through Water Coordination -- 3.1.2 Lanthanides in Aqueous-phase Catalysis -- 3.1.2.1 Introduction -- 3.1.2.2 Aldol Reactions -- 3.1.2.3 Mannich-type Reactions -- 3.1.2.4 Diels - Alder Reactions -- 3.1.2.5 Micellar Systems -- 3.1.2.6 Asymmetric Catalysis in Aqueous Media. , 3.1.2.7 Conclusions -- 3.2 Variation of Ligands -- 3.2.1 Monophosphines -- 3.2.1.1 General Features, Scope, and Limitations -- 3.2.1.2 Anionic Phosphines -- 3.2.1.3 Cationic Phosphines -- 3.2.1.4 Nonionic Water-soluble Phosphines -- 3.2.2 Diphosphines and Other Phosphines -- 3.2.2.1 General -- 3.2.2.2 Diphosphines - Introduction of Sulfonate Groups by Direct Sulfonation -- 3.2.2.3 Introduction of Sulfonate Groups During Synthesis -- 3.2.2.4 Diphosphines with Quaternized Aminoalkyl or Aminoaryl Groups -- 3.2.2.5 Diphosphines with Hydroxyalkyl or Polyether Substituents -- 3.2.2.6 Carboxylated Diphosphines -- 3.2.2.7 Amphiphilic Diphosphines -- 3.2.2.8 Other Phosphines -- 3.2.3 Ligands or Complexes Containing Ancillary Functionalities -- 3.2.3.1 Complexes Containing at Least Two Classical Functionalities -- 3.2.3.2 Cationic Complexes -- 3.2.3.3 Immobilization on Silica Supports -- 3.2.3.4 Macromolecular Ligands or Supports -- 3.2.3.5 Ligands not Containing Phosphorus -- 3.2.3.6 Additional Perspectives -- 3.2.4 Tenside Ligands -- 3.2.4.1 Introduction -- 3.2.4.2 Tenside Phosphines and Amines -- 3.2.4.3 Hydroformylation Reactions Catalyzed by Transition Metal Surfactant - Phosphine Complexes -- 3.2.4.4 Hydrogenation Reactions Catalyzed by Transition Metal Surfactant - Phosphine Complexes -- 3.2.4.5 Carbonylation Reactions Catalyzed by Transition Metal Surfactant - Phosphine Complexes -- 3.2.4.6 Concluding Remarks and Future Prospects -- 3.2.5 Chiral Ligands -- 3.2.5.1 Introduction -- 3.2.5.2 Sulfonated Chiral Phosphines -- 3.2.5.3 Other Water-soluble Chiral Ligands -- 3.2.5.4 Conclusions -- 3.2.6 Other Concepts -- 3.2.6.1 Hydroxyphosphines as Ligands -- 3.2.6.2 Amines and Polyoxometallates as Ligands -- 4 Catalysis in Water as a Special Unit Operation -- 4.1 Fundamentals of Biphasic Reactions in Water -- 4.1.1 Introduction. , 4.1.2 Gas/Liquid-phase Reactions -- 4.1.3 Gas/Liquid/Liquid-phase Reactions -- 4.1.4 Place of Reaction in Aqueous Biphasic Systems -- 4.2 Technical Concepts -- 4.2.1 Reaction Systems -- 4.2.2 Technical Realization: Variations -- 4.2.2.1 Reaction with Product Separation -- 4.2.2.2 Reaction and Product Extraction -- 4.2.2.3 Reaction and Product Treatment -- 4.2.2.4 Reaction and Catalyst Separation -- 4.2.2.5 Reaction and Catalyst Extraction -- 4.2.2.6 Reaction and Catalyst Treatment -- 4.2.3 Reaction Engineering Aspects -- 4.2.4 New Developments -- 4.2.4.1 Telomerization -- 4.2.4.2 Oligomerization -- 4.2.4.3 Hydrogenation -- 4.2.4.4 Hydroformylation -- 4.2.4.5 Other Reactions -- 4.3 Side Effects, Solvents, and Co-solvents -- 4.3.1 Introduction -- 4.3.2 Hydroformylation -- 4.3.3 Hydrogenations and Other Catalytic Reactions -- 4.4 Membrane Techniques -- 4.5 Micellar Systems -- 4.5.1 Introduction -- 4.5.2 Hydrolytic Reactions in Micelles -- 4.5.3 Oxidation Reactions in Micelles -- 4.5.4 Complex-catalyzed Hydrogenation in Micellar Media -- 4.5.5 Carbon-Carbon Coupling Systems -- 4.5.6 Some Examples of Reactions in Reverse Micelles and Microemulsions -- 4.5.7 Perspectives -- 4.6 On the Borderline of Aqueous-phase Catalysis -- 4.6.1 Phase-transfer Catalysis -- 4.6.1.1 General Overview, Fundamentals, and Definitions -- 4.6.1.2 Aqueous Organic-phase Heck and Other Cross Couplings under Phase-transfer Catalysis Conditions -- 4.6.1.3 Hydrogenations Mediated by Phase-transfer Catalysts -- 4.6.1.4 Biphasic Transfer Hydrogenations -- 4.6.1.5 Aqueous/Organic-phase Oxidations Mediated by Metal and PT Catalysts -- 4.6.1.6 Aqueous/Organic-phase Carbonylations -- 4.6.2 Counter-phase Transfer Catalysis -- 4.6.2.1 Introduction -- 4.6.2.2 Mechanism of the Counter-phase Transfer Catalytic Reaction -- 4.6.2.3 Counter-phase Transfer Catalytic Reactions. , 4.6.2.4 Concluding Remarks -- 4.6.3 Thermoregulated Phase-transfer and Thermoregulated Phase-separable Catalysis -- 4.6.3.1 Introduction -- 4.6.3.2 Thermoregulated Phase-transfer Catalysis with Nonionic Water-soluble Phosphines -- 4.6.3.3 Hydroformylation of Higher Alkenes Based on TRPTC -- 4.6.3.4 Thermoregulated Phase-separable Catalysis -- 4.6.3.5 Conclusions -- 4.7 Transitions to Heterogeneous Techniques (SAPC and Variations) -- 4.7.1 Introduction -- 4.7.2 The SAPC Concept of Immobilization -- 4.7.3 Example of Rational Catalyst Design Strategy -- 4.7.4 Suggested Reactions for Implementation of Design Concepts -- 4.7.5 Outlook -- 5 Aqueous Catalysts for Environment and Safety -- 5.1 Water-soluble Organometallics in the Environment -- 5.1.1 Introduction -- 5.1.2 Biological Methylation -- 5.1.3 Cobalamines - Organometallics in Nature -- 5.1.4 Organoarsenic and Organotin Compounds -- 5.1.5 Organomercury Compounds -- 5.1.6 Other Metal-alkyl Complexes in the Environment -- 5.1.7 Perspectives -- 5.2 Environmental and Safety Aspects -- 5.2.1 Introduction -- 5.2.2 The Ruhrchemie/Rhône-Poulenc (RCH/RP) Process -- 5.2.3 Crucial Environmental Improvements -- 5.2.4 Conclusions -- 6 Typical Reactions -- 6.1 Hydroformylation -- 6.1.1 Development of the Commercial Biphasic Oxo Synthesis -- 6.1.1.1 History of Biphasic Catalysis -- 6.1.1.2 Basic Work and Investigations by Rhône-Poulenc -- 6.1.1.3 Investigations by Ruhrchemie AG -- 6.1.1.4 The RCH/RP Process as the Final Point of Development -- 6.1.2 Kinetics -- 6.1.2.1 Introduction -- 6.1.2.2 Kinetics Using Water-soluble Catalysts -- 6.1.2.3 Concluding Remarks -- 6.1.3 Reaction of Alkenes -- 6.1.3.1 Lower Alkenes -- 6.1.3.2 Higher Alkenes -- 6.1.3.3 Functionalized Alkenes -- 6.1.4 Re-immobilization Techniques -- 6.1.4.1 Introduction. , 6.1.4.2 Water-insoluble, Re-immobilized Liphophilic Ligands and Their Separation by Membrane Technique -- 6.1.4.3 Separation and Use of Water-insoluble Ammonium Ligands in Hydroformylation -- 6.1.4.4 Separation of Phosphine Oxides and Other Degradation Products -- 6.1.4.5 Further Developments -- 6.2 Hydrogenation -- 6.2.1 Introduction -- 6.2.2 Mechanisms and Catalysts of Hydrogenations in Aqueous Solution -- 6.2.2.1 Basic Mechanisms of Dihydrogen Activation -- 6.2.2.2 Water-soluble Hydrogenation Catalysts with Tertiary Phosphine Ligands -- 6.2.2.3 Complexes of Ligands with Donor Atoms Other Than Phosphorus(III ) -- 6.2.3 Typical Reactions -- 6.2.3.1 Hydrogenation of Compounds with C=C and C≡C Bonds -- 6.2.3.2 Hydrogenation of Compounds with C=O and C=N Bonds -- 6.2.3.3 Hydrogenolysis of C-O, C-N, C-S, and C-Halogen Bonds -- 6.2.3.4 Miscellaneous Hydrogenations -- 6.3 Hydrogenation and Hydrogenolysis of Thiophenic Molecules -- 6.3.1 Introduction -- 6.3.2 Hydrogenation Reactions -- 6.3.3 Hydrogenolysis Reactions -- 6.3.4 Future Developments -- 6.4 Oxidations -- 6.4.1 Partial Oxidations -- 6.4.1.1 Introduction -- 6.4.1.2 Water-soluble Ligands -- 6.4.1.3 Concluding Remarks -- 6.4.2 Wacker-type Oxidations -- 6.4.2.1 Possibilities of Wacker-type Oxidations -- 6.4.2.2 Conclusions -- 6.4.3 Methyltrioxorhenium(VII) as an Oxidation Catalyst -- 6.4.3.1 Introduction -- 6.4.3.2 Synthesis of Methyltrioxorhenium(VII) -- 6.4.3.3 Behavior of Methyltrioxorhenium in Water -- 6.4.3.4 Catalyst Formation and Applications in Alkene Epoxidation -- 6.4.3.5 Other Oxidation Reactions -- 6.4.3.6 Perspectives -- 6.5 Carbonylation Reactions -- 6.5.1 Introduction -- 6.5.2 Reductive Carbonylations -- 6.5.3 Carboxylation of C-X Derivatives -- 6.5.4 Hydrocarboxylation of Alkenes -- 6.5.5 Conclusions -- 6.6 C-C Coupling Reactions (Heck, Stille, Suzuki, etc.) -- 6.6.1 Introduction. , 6.6.2 Catalysts and Reaction Conditions.

Note: Intro -- Title Page -- Copyright -- List of Contributors -- Preface to the Third Edition -- Chapter 1: Introduction -- 1.1 Historical Pathways -- 1.2 Topical Developments Since Year 2000 -- 1.3 Organization of the Third Edition -- 1.4 Historical Glossary -- References -- Part A: Applied Homogeneous Catalysis -- Chapter 2: Hydroformylation -- 2.1 General Aspects -- 2.2 Conventional Processes -- 2.3 Aqueous-Phase Process -- References -- Chapter 3: Carbonylation -- 3.1 Carbonylation: Introduction and General Aspects -- 3.2 Carbonylation of Methanol and its Derivatives to Acetic Acid and Acetic Anhydride -- 3.3 Alkyne Carbonylation -- 3.4 Aryl-X and Related Carbonylations -- 3.5 Transition Metal-Catalyzed Oxidative Carbonylations -- 3.6 Alternating Copolymerization with Carbon Monoxide -- References -- Chapter 4: Polymerization and Copolymerization -- 4.1 General Aspects -- 4.2 Metallocene-Catalyzed Polyolefins -- 4.3 Post- and Non-metallocenes for Olefin Insertion Polymerization -- 4.4 Polymerization of 1,3-Butadiene with Organometallic Complexes-Based Catalysts -- 4.5 Polycarbonates -- References -- Chapter 5: Oligomerization, Cyclooligomerization, Dimerization -- 5.1 Selective Production of 1-Hexene and 1-Octene -- 5.2 Dimerization and Selective Oligomerization - Selected Examples of Industrial Applications -- 5.3 Telomerization of 1,3-Butadiene -- 5.4 Cyclotrimerization Reactions of Alkynes -- Abbreviations -- References -- Chapter 6: Cross Coupling Reactions -- 6.1 Coupling Reactions: Introduction and General Aspects -- 6.2 Industrial Applications of Palladium-Catalyzed Coupling Reactions -- 6.3 Ligand-Enabled Palladium-Catalyzed C-N and C-O Bond Formations from Aryl Halides, Tosylates and Mesylates -- References -- Chapter 7: Oxidation -- 7.1 General Aspects -- 7.2 Aromatic Carboxylic Acids. , 7.3 Oxidation of Olefins to Carbonyl Compounds (Wacker Process) -- 7.4 Radical Chain Oxidations -- 7.5 Manganese and Iron Bleaching Catalysts -- 7.6 Catalytic Decarbonylative and Decarboxylative Processes -- 7.7 Oxidation of Phenols -- References -- Chapter 8: Hydrosilylation and Related Reactions of Silicon Compounds -- 8.1 Introduction -- 8.2 Hydrosilylation of Carbon-Carbon Multiple Bonds -- 8.3 Chemo- and Enantioselective Hydrosilylation of Unsaturated Carbon-Heteroatom Bonds -- 8.4 Silicometallics and Catalysis -- References -- Chapter 9: Hydrogenation -- 9.1 Industrial Application of Asymmetric Hydrogenation -- 9.2 Hydrogenation of Esters -- Abbreviations -- References -- Part B: Recent Developments -- Subpart 1: Catalysts -- Chapter 10: New Trends in Organometallic Catalysts -- 10.1 Iron Catalysis -- 10.2 Copper-Catalyzed Arylation of Nucleophiles: History, Renaissance and Scalable Reactions -- 10.3 Rare Earth Metal Catalysts -- 10.4 Chiral Frustrated Lewis Pair Catalysts -- References -- Chapter 11: New Ligands -- 11.1 N-Heterocyclic Carbenes -- 11.2 Phosphorus Ligands in Homogeneous Catalysis -- 11.3 Host-Guest Relations and Self-Organization in Homogeneous Catalysis -- 11.4 Micellar Catalysis -- 11.5 Switchable Catalysis -- 11.6 Catalysis with Transition Metal Pincer Complexes -- 11.7 Biocatalysis -- References -- Subpart 2: Methods -- Chapter 12: Computational Investigations into the Heck Type Reaction Mechanisms -- 12.1 Introduction -- 12.2 Oxidative Addition -- 12.3 Regioselectivity -- 12.4 Stereoselectivity -- 12.5 Alternative Mechanism Involving a Pd(II/IV) Redox System -- 12.6 Concluding Remarks -- References -- Chapter 13: Chemical Reaction Engineering Aspects of Homogeneously Catalyzed Processes -- 13.1 Introduction -- 13.2 Kinetics in Homogeneous Catalysis -- 13.3 Aspects of Catalyst Recycling -- 13.4 Symbols -- References. , Chapter 14: Supported Liquid Phase Catalysis -- 14.1 Introduction -- 14.2 Support Materials -- 14.3 Thin Film Coating Materials -- 14.4 Summary and Outlook -- References -- Chapter 15: Recent Advances in Surface Organometallic Chemistry -- 15.1 Introduction -- 15.2 Strategy and Methods -- 15.3 A Decade of Development of Single-Site Heterogeneous Catalysts -- 15.4 New Directions -- 15.5 Challenges and Perspectives -- References -- Chapter 16: High Throughput Screening of Homogeneous Catalysts: Selected Trends and Applications in Process Development -- 16.1 Summary -- References -- Chapter 17: Homogeneous Photocatalysis with Organometallic Compounds -- 17.1 Introduction -- 17.2 Metal Carbonyl Catalyzed Reactions -- 17.3 Copper (I) Catalyzed [2+2] Photocycloadditions of Alkenes -- 17.4 Photochemical Electron Transfer Mediated Reactions -- 17.5 Photochemically Supported C-H Activation with Organometal Compounds -- 17.6 Conclusions -- References -- Chapter 18: Electrochemical Water Oxidation and Reduction Catalyzed by Organometallic Compounds -- 18.1 Introduction -- 18.2 Electrochemical Water Oxidation to O2 Catalyzed by Organometallic Compounds -- 18.3 Electrochemical Water Reduction to H2 Catalyzed by Organometallic Compounds -- 18.4 Concluding Remarks and Outlook -- References -- Chapter 19: Metal-Catalyzed Multicomponent Reactions -- 19.1 Introduction -- 19.2 Multicomponent Carbonylation Reactions -- 19.3 Multicomponent Cross-Coupling Reactions -- 19.4 Metallacycles in Multicomponent Reactions -- 19.5 Multicomponent Approaches to 1,3-Dipolar Cycloadditions -- 19.6 Summary and Outlook -- References -- Chapter 20: Supercritical Fluids as Advanced Media for Reaction and Separation in Homogeneous Catalysis -- 20.1 Introduction -- 20.2 Organometallic Catalysis in Supercritical Fluids -- 20.3 Organometallic Catalysis in CO2-Expanded Liquid Phases. , 20.4 Supercritical CO2-Based Multiphase Systems for Continuous-Flow Homogeneous Catalysis -- 20.5 Summary and Outlook -- References -- Subpart 3: Special Reactions -- Chapter 21: Carbonylation of Nitroarenes and Aromatic Amines -- 21.1 Present Synthesis of Isocyanates via the Phosgene Route -- 21.2 Alternative Carbonylation Strategies towards Carbonic Acid Derivatives -- 21.3 Overview -- 21.4 Reductive Carbonylation of Nitroarenes -- 21.5 Redox Carbonylation of Nitroarenes and Aromatic Amines According to (21.4) and (21.5) -- 21.6 Oxidative Carbonylation of Aromatic Amines According to (21.6) and (21.7) -- 21.7 Summary -- References -- Chapter 22: Pauson-Khand Reaction -- 22.1 Introduction -- 22.2 Co-Catalyzed Reaction -- 22.3 Ti-Catalyzed Reaction -- 22.4 Ru-Catalyzed Reaction -- 22.5 Rh-Catalyzed Reaction -- 22.6 Ir-Catalyzed Reaction -- 22.7 Summary -- References -- Chapter 23: C-H Activation Coupling Reactions -- 23.1 Introduction -- 23.2 Mechanisms of C-H Bond Activation -- 23.3 Selectivity of Competitive C-H Bond Activations -- 23.4 Functionalization of Alkanes and C(sp3)-H Bonds -- 23.5 Aromatic C-H Transformations -- 23.6 Alkylation of Nitrogen Heterocycles -- 23.7 Hydroacylation of Alkenes and Alkynes -- 23.8 Summary and Outlook -- References -- Chapter 24: Metathesis -- 24.1 Historical Background (Introduction) -- 24.2 Reaction Mechanism -- 24.3 Homogeneous Catalytic Systems -- 24.4 Industrial Applications -- 24.5 Conclusion -- Acknowledgments -- References -- Chapter 25: The Value and Application of Transition Metal Catalyzed Alkene Isomerization in Industry -- 25.1 Introductory Remarks and Mechanistic Considerations -- 25.2 Isomerization of Non-functionalized Alkenes -- 25.3 Isomerization of Functionalized Alkenes -- 25.4 Recent Developments -- 25.5 Concluding Remarks -- References. , Chapter 26: Catalysis and Scope of the Hydroamination of Non-activated CC Multiple Bonds -- 26.1 Introduction -- 26.2 Rare-Earth and Actinide Metals as Hydroamination Catalysts -- 26.3 Hydroamination Catalysts Based on Group 4/5 Metals -- 26.4 Hydroamination Catalysts Based on Alkaline-Earth Metals -- 26.5 Late Transition-Metal Complexes as Homogeneous Hydroamination Catalysts -- 26.6 Heterogeneous and Immobilized Hydroamination Catalysts -- 26.7 Brønsted Acid Catalyzed Hydroamination of Alkenes and Alkynes -- 26.8 Base-Catalyzed Hydroamination -- 26.9 Conclusions -- Acknowledgments -- References -- Chapter 27: Catalytic Amide Bond Forming Methods -- 27.1 Amidation of Carboxylic Acids -- 27.2 Transamidation -- 27.3 Amidation of Esters -- 27.4 Amidation of Aldehydes (Without Oxime Intermediates) -- 27.5 Amidation of Alcohols -- 27.6 Amidation of Nitriles -- 27.7 Oxime/Oxime Intermediates to Amides -- 27.8 Aminocarbonylations -- 27.9 Miscellaneous Amidations -- 27.10 Conclusion -- References -- Chapter 28: Synthesis of Heterocycles by Pd-catalyzed and Pd-catalysis Initiated Multi-component Reactions -- 28.1 Introduction -- 28.2 MCR by Insertion of Allenes -- 28.3 MCR by Insertion of Carbon Monoxide -- 28.4 MCR by Insertion of Alkenes and Alkynes -- 28.5 MCR by Initial Sonogashira Alkynylation -- 28.6 MCR by Carbonylative Sonogashira Alkynylation -- 28.7 MCR by Catalytic Enamine Generation and Arylation -- 28.8 Conclusion -- List of Abbreviations -- Acknowledgments -- References -- Chapter 29: Metal-Catalyzed Baeyer-Villiger Oxidations -- 29.1 Introduction -- 29.2 Oxidation of Cyclobutanones -- 29.3 Oxidation of Other Ketones -- 29.4 BV in Water -- 29.5 Organic and Heterogeneous Catalysis -- 29.6 Conclusions -- References -- Chapter 30: Dihydroxylations of Olefins and Related Reactions -- 30.1 Introduction -- 30.2 Osmium -- 30.3 Ruthenium -- 30.4 Iron. , References.

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