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Palladium-Catalyzed Coupling Reactions: InhaltsangabeForeword XIIIPreface XVList of Contributors XVII1 Palladium-Catalyzed Cross-Coupling Reactions &ndash A General Introduction 1 Klaus K&euro ohler, Katharina Wussow, and Andreas Sebastian Wirth1.1 Introduction 11.1.1 Historical Reflection 11.1.2 Characteristics, Recent Developments, and Progress 21.1.3 Literature Reviews and Organization of the Chapter 31.2 Carbon&ndash Carbon Cross-Coupling Reactions Catalyzed by Palladium 41.2.1 Classification and Overview 41.2.2 Common Mechanistic Features of Cross-Coupling Reactions and Reactivity of the Substrates 81.2.2.1 Choice of the Carbon Electrophile 91.2.2.2 Choice of the Carbon Nucleophile &ndash What Makes the Difference 91.3 The Catalysts 101.3.1 The Particular Features of Palladium 101.3.2 Classes of Palladium Catalysts Applied to Cross-Coupling Reactions 121.3.2.1 Ligands and Palladium Complexes &ndash Homogeneous Systems 131.3.2.2 Immobilized or Supported Palladium Complexes and Particles &ndash Heterogeneous Systems 171.3.2.3 Palladium Colloids and (Nonsupported) Nanoparticles 171.3.2.4 Activity of Heterogeneous Catalysts 181.4 Mechanistic Aspects 181.4.1 General Mechanism of CC Cross-Coupling and Heck Reactions with Homogeneous Catalyst Precursors 181.4.2 Models for Heck and Suzuki Reactions with Supported Pd Precursors 191.4.3 Recent Results on the Reaction Mechanism and the Nature of the Active Pd Species 211.4.3.1 Observation of Intermediates in Homogeneous Catalysis by Electrochemical Methods 211.4.3.2 The Question of Pd Leaching 221.4.3.3 Selectivity Pattern 231.4.3.4 In Situ Observation by Spectroscopic Methods 241.4.3.5 Immobilized Pd Pincer Complexes 241.4.3.6 Palladium Bulk Materials (Pd Foil, Wire, Sponge) as Catalyst 241.5 Future Challenges 25Abbreviations 27References 272 High-Turnover Heterogeneous Palladium Catalysts in Coupling Reactions: the Case of Pd Loaded on Dealuminated Y Zeolites 31 Kazu Okumura2.1 Introduction 312.2 Various Methodologies to Afford High Turnover Numbers Over Supported Pd Catalysts 322.3 Structure and Characteristics of Ultrastable Y Zeolites 332.4 Suzuki&ndash Miyaura Reactions Catalyzed by Pd/USY 352.4.1 Catalytic Performance of Pd/USY 352.4.2 Pd Leaching from Pd/USY 402.4.3 Selectivity in the Homocoupling Reactions 412.4.4 Characterization of the Active Pd Species by X-Ray Absorption Spectroscopy 412.4.5 A Suggested Mechanism for the Formation of Active Pd Species in Suzuki&ndash Miyaura Coupling Reactions 462.5 Catalytic Performance of Pd/USY in Mizoroki&ndash Heck Reactions 482.5.1 Effect of H2 Bubbling on the Catalytic Reactions of Pd/USY 482.5.2 Catalytic Reactions Using Chlorobenzene Derivatives 512.5.3 Characterization of the Pd Species by X-Ray Absorption Spectroscopy 532.6 Conclusion and Perspective 54Abbreviations 55References 553 Palladium-Catalyzed Coupling Reactions with Magnetically Separable Nanocatalysts 57 Kifah S.M. Salih and Werner R. Thiel3. Nonsiliceous Solids 1214.3.4.1 Metal&ndash Organic Frameworks 1214.3.4.2 Covalent Organic Frameworks 1234.3.4.3 Other Support Materials 1244.4 Miscellaneous Coupling Reactions 1274.5 The Question of Solution-Phase Catalysis 1304.6 Summary and Future Prospects 131Abbreviations 133References 1345 Coupling Reactions Induced by Polymer-Supported Catalysts 141 Babak Karimi, Sedigheh Abedi, and Asghar Zamani5.1 Introduction 1415.2 Polysaccharides 1435.2.1 Starch 1435.2.2 Chitosan 1455.2.3 Other Polysaccharides 1485.3 Poly(ethylene glycol) 1505.3.1 Nonfunctionalized Poly(ethylene glycol) 1505.3.2 Functionalized Poly(ethylene glycol) 1525.4 Polystyrene 1555.4.1 Nonfunctionalized Polystyrene 1555.4.2 Functionalized Polystyrene 1565.4.2.1 Polystyrene-Supported Ligands Containing Nitrogen 1565.4.2.2 Polystyrene-Supported Triphenylphosphane 1615.5 Poly(norbornene) 1655.6 Polyacrylamide 1675.7 Polyaniline 1705.8 Poly(N-vinyl-2-pyrrolidone) 1715.9 Polypyrrole 1735.10 Poly(4-vinylpyridine) 1745.11 Ionic Polymers 1755.11.1 Organic Polymers Containing N-Heterocyclic Carbenes or Ionic Liquids 1765.11.2 Polymers Containing Other Ionic Ligands 1835.12 Organometallic Polymers 1845.13 Functionalized Porous Organic Polymers 1885.14 Miscellaneous Polymers 1895.15 Summary and Outlook 192Abbreviations 193References 1956 Coupling Reactions in Ionic Liquids 201 Michael T. Ke&szlig ler, Jackson D. Scholten, Frank Galbrecht, and Martin H.G. Prechtl6.1 Introduction 2016.2 Metal Complexes 2046.2.1 Mizoroki&ndash Heck Reaction 2056.2.2 Sonogashira Coupling 2096.2.3 Suzuki&ndash Miyaura Coupling 2126.2.4 Negishi Coupling 2136.2.5 Trost&ndash Tsuji Coupling 2146.3 Metal Salts and Metal on Solid Support 2146.3.1 Mizoroki&ndash Heck Reaction 2156.3.2 Suzuki&ndash Miyaura Reaction 2186.3.3 Stille Reaction 2196.4 Metal Nanoparticles 2206.4.1 The Mizoroki&ndash Heck Reaction with PdNPs in ILs 2226.4.2 Suzuki&ndash Miyaura Reaction 2246.4.3 Stille Reaction 2266.4.4 Buchwald&ndash Hartwig Reaction 2276.4.5 Sonogashira Reaction 2286.4.6 Ullmann Reaction 2286.5 Summary and Outlook 229Abbreviations 230References 2317 Cross-Coupling Reactions in Aqueous Media 235 Kevin H. Shaughnessy7.1 Introduction 2357.2 Cross-Coupling of Organic Halides to Form CC Bonds in Aqueous Media 2367.2.1 Suzuki Coupling 2367.2.1.1 Aqueous-Phase Suzuki Coupling Using Hydrophilic Ligand-Supported Catalysts 2377.2.1.2 On Water Suzuki Couplings with Hydrophobic Catalyst Systems 2487.2.1.3 Surfactant-Promoted Aqueous-Phase Suzuki Couplings 2497.2.1.4 Palladium Catalysts Supported on Heterogeneous Supports 2517.2.1.5 Palladium Nanoparticle Cata 3088.2.4 Coupling of Terminal Alkynes with Aryl Halides 3108.2.5 Coupling Reactions of Organostannanes with Organic Halides 3128.2.6 Couplings of Organosilanes with Aryl Halides 3138.2.7 Cyanation of Aryl Halides 3158.2.8 Carbonylation Reactions 3168.2.9 Decarboxylative Couplings 3188.2.10 Other CC Bond Formations 3198.3 CX Bond Formation 3218.3.1 CN Bond Formation 3218.3.2 CP Bond Formation 3258.4 Conclusions 327Abbreviations 327References 3289 Catalyst Recycling in Palladium-Catalyzed Carbon&ndash Carbon Coupling Reactions 333 Arpad Molnar9.1 Introduction 3339.2 General Issues of Catalyst Recycling 3339.3 Catalyst Systems Providing High, Consistent Yields in Recycling 3379.3.1 The Use of Catalysts with Pd Particles 3379.3.2 Recycling of Palladium Complexes 3469.3.2.1 Complexes Anchored to Inorganic Supports 3469.3.2.2 Complexes Immobilized on Polymers 3559.3.2.3 Self-Supported Polymeric Complexes 3619.3.3 Studies Performed Under Homogeneous Conditions 3629.4 Catalysts Affording the Highest Cumulative TON Values in Recycling Studies 3709.4.1 Catalysts with Supported Particles 3709.4.2 Immobilized Complexes 3739.5 Summary Evaluation 3759.6 Future Outlook 381Abbreviations 382References 38310 Nature of the True Catalytic Species in Carbon&ndash Carbon Coupling Reactions with Heterogeneous Palladium Precatalysts 387 Lin Huang and Pui Kwan Wong10.1 Introduction 38710.2 Heck Reactions 38910.2.1 Supported Pd Particles 38910.2.2 Immobilized Pd Complexes 39410.3 Suzuki Reactions 39610.3.1 Supported Pd Particles, Englisch, Ebook.

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Palladium-Catalyzed Coupling Reactions: InhaltsangabeForeword XIIIPreface XVList of Contributors XVII1 Palladium-Catalyzed Cross-Coupling Reactions &ndash A General Introduction 1 Klaus K&euro ohler, Katharina Wussow, and Andreas Sebastian Wirth1.1 Introduction 11.1.1 Historical Reflection 11.1.2 Characteristics, Recent Developments, and Progress 21.1.3 Literature Reviews and Organization of the Chapter 31.2 Carbon&ndash Carbon Cross-Coupling Reactions Catalyzed by Palladium 41.2.1 Classification and Overview 41.2.2 Common Mechanistic Features of Cross-Coupling Reactions and Reactivity of the Substrates 81.2.2.1 Choice of the Carbon Electrophile 91.2.2.2 Choice of the Carbon Nucleophile &ndash What Makes the Difference 91.3 The Catalysts 101.3.1 The Particular Features of Palladium 101.3.2 Classes of Palladium Catalysts Applied to Cross-Coupling Reactions 121.3.2.1 Ligands and Palladium Complexes &ndash Homogeneous Systems 131.3.2.2 Immobilized or Supported Palladium Complexes and Particles &ndash Heterogeneous Systems 171.3.2.3 Palladium Colloids and (Nonsupported) Nanoparticles 171.3.2.4 Activity of Heterogeneous Catalysts 181.4 Mechanistic Aspects 181.4.1 General Mechanism of CC Cross-Coupling and Heck Reactions with Homogeneous Catalyst Precursors 181.4.2 Models for Heck and Suzuki Reactions with Supported Pd Precursors 191.4.3 Recent Results on the Reaction Mechanism and the Nature of the Active Pd Species 211.4.3.1 Observation of Intermediates in Homogeneous Catalysis by Electrochemical Methods 211.4.3.2 The Question of Pd Leaching 221.4.3.3 Selectivity Pattern 231.4.3.4 In Situ Observation by Spectroscopic Methods 241.4.3.5 Immobilized Pd Pincer Complexes 241.4.3.6 Palladium Bulk Materials (Pd Foil, Wire, Sponge) as Catalyst 241.5 Future Challenges 25Abbreviations 27References 272 High-Turnover Heterogeneous Palladium Catalysts in Coupling Reactions: the Case of Pd Loaded on Dealuminated Y Zeolites 31 Kazu Okumura2.1 Introduction 312.2 Various Methodologies to Afford High Turnover Numbers Over Supported Pd Catalysts 322.3 Structure and Characteristics of Ultrastable Y Zeolites 332.4 Suzuki&ndash Miyaura Reactions Catalyzed by Pd/USY 352.4.1 Catalytic Performance of Pd/USY 352.4.2 Pd Leaching from Pd/USY 402.4.3 Selectivity in the Homocoupling Reactions 412.4.4 Characterization of the Active Pd Species by X-Ray Absorption Spectroscopy 412.4.5 A Suggested Mechanism for the Formation of Active Pd Species in Suzuki&ndash Miyaura Coupling Reactions 462.5 Catalytic Performance of Pd/USY in Mizoroki&ndash Heck Reactions 482.5.1 Effect of H2 Bubbling on the Catalytic Reactions of Pd/USY 482.5.2 Catalytic Reactions Using Chlorobenzene Derivatives 512.5.3 Characterization of the Pd Species by X-Ray Absorption Spectroscopy 532.6 Conclusion and Perspective 54Abbreviations 55References 553 Palladium-Catalyzed Coupling Reactions with Magnetically Separable Nanocatalysts 57 Kifah S.M. Salih and Werner R. Thiel3. Nonsiliceous Solids 1214.3.4.1 Metal&ndash Organic Frameworks 1214.3.4.2 Covalent Organic Frameworks 1234.3.4.3 Other Support Materials 1244.4 Miscellaneous Coupling Reactions 1274.5 The Question of Solution-Phase Catalysis 1304.6 Summary and Future Prospects 131Abbreviations 133References 1345 Coupling Reactions Induced by Polymer-Supported Catalysts 141 Babak Karimi, Sedigheh Abedi, and Asghar Zamani5.1 Introduction 1415.2 Polysaccharides 1435.2.1 Starch 1435.2.2 Chitosan 1455.2.3 Other Polysaccharides 1485.3 Poly(ethylene glycol) 1505.3.1 Nonfunctionalized Poly(ethylene glycol) 1505.3.2 Functionalized Poly(ethylene glycol) 1525.4 Polystyrene 1555.4.1 Nonfunctionalized Polystyrene 1555.4.2 Functionalized Polystyrene 1565.4.2.1 Polystyrene-Supported Ligands Containing Nitrogen 1565.4.2.2 Polystyrene-Supported Triphenylphosphane 1615.5 Poly(norbornene) 1655.6 Polyacrylamide 1675.7 Polyaniline 1705.8 Poly(N-vinyl-2-pyrrolidone) 1715.9 Polypyrrole 1735.10 Poly(4-vinylpyridine) 1745.11 Ionic Polymers 1755.11.1 Organic Polymers Containing N-Heterocyclic Carbenes or Ionic Liquids 1765.11.2 Polymers Containing Other Ionic Ligands 1835.12 Organometallic Polymers 1845.13 Functionalized Porous Organic Polymers 1885.14 Miscellaneous Polymers 1895.15 Summary and Outlook 192Abbreviations 193References 1956 Coupling Reactions in Ionic Liquids 201 Michael T. Ke&szlig ler, Jackson D. Scholten, Frank Galbrecht, and Martin H.G. Prechtl6.1 Introduction 2016.2 Metal Complexes 2046.2.1 Mizoroki&ndash Heck Reaction 2056.2.2 Sonogashira Coupling 2096.2.3 Suzuki&ndash Miyaura Coupling 2126.2.4 Negishi Coupling 2136.2.5 Trost&ndash Tsuji Coupling 2146.3 Metal Salts and Metal on Solid Support 2146.3.1 Mizoroki&ndash Heck Reaction 2156.3.2 Suzuki&ndash Miyaura Reaction 2186.3.3 Stille Reaction 2196.4 Metal Nanoparticles 2206.4.1 The Mizoroki&ndash Heck Reaction with PdNPs in ILs 2226.4.2 Suzuki&ndash Miyaura Reaction 2246.4.3 Stille Reaction 2266.4.4 Buchwald&ndash Hartwig Reaction 2276.4.5 Sonogashira Reaction 2286.4.6 Ullmann Reaction 2286.5 Summary and Outlook 229Abbreviations 230References 2317 Cross-Coupling Reactions in Aqueous Media 235 Kevin H. Shaughnessy7.1 Introduction 2357.2 Cross-Coupling of Organic Halides to Form CC Bonds in Aqueous Media 2367.2.1 Suzuki Coupling 2367.2.1.1 Aqueous-Phase Suzuki Coupling Using Hydrophilic Ligand-Supported Catalysts 2377.2.1.2 On Water Suzuki Couplings with Hydrophobic Catalyst Systems 2487.2.1.3 Surfactant-Promoted Aqueous-Phase Suzuki Couplings 2497.2.1.4 Palladium Catalysts Supported on Heterogeneous Supports 2517.2.1.5 Palladium Nanoparticle Cata 3088.2.4 Coupling of Terminal Alkynes with Aryl Halides 3108.2.5 Coupling Reactions of Organostannanes with Organic Halides 3128.2.6 Couplings of Organosilanes with Aryl Halides 3138.2.7 Cyanation of Aryl Halides 3158.2.8 Carbonylation Reactions 3168.2.9 Decarboxylative Couplings 3188.2.10 Other CC Bond Formations 3198.3 CX Bond Formation 3218.3.1 CN Bond Formation 3218.3.2 CP Bond Formation 3258.4 Conclusions 327Abbreviations 327References 3289 Catalyst Recycling in Palladium-Catalyzed Carbon&ndash Carbon Coupling Reactions 333 Arpad Molnar9.1 Introduction 3339.2 General Issues of Catalyst Recycling 3339.3 Catalyst Systems Providing High, Consistent Yields in Recycling 3379.3.1 The Use of Catalysts with Pd Particles 3379.3.2 Recycling of Palladium Complexes 3469.3.2.1 Complexes Anchored to Inorganic Supports 3469.3.2.2 Complexes Immobilized on Polymers 3559.3.2.3 Self-Supported Polymeric Complexes 3619.3.3 Studies Performed Under Homogeneous Conditions 3629.4 Catalysts Affording the Highest Cumulative TON Values in Recycling Studies 3709.4.1 Catalysts with Supported Particles 3709.4.2 Immobilized Complexes 3739.5 Summary Evaluation 3759.6 Future Outlook 381Abbreviations 382References 38310 Nature of the True Catalytic Species in Carbon&ndash Carbon Coupling Reactions with Heterogeneous Palladium Precatalysts 387 Lin Huang and Pui Kwan Wong10.1 Introduction 38710.2 Heck Reactions 38910.2.1 Supported Pd Particles 38910.2.2 Immobilized Pd Complexes 39410.3 Suzuki Reactions 39610.3.1 Supported Pd Particles, Englisch, Ebook.

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This handbook and ready reference brings together all significant issues of practical importance for interested readers in one single volume. While covering homogeneous and heterogeneous catalysis, the text is unique in focusing on such important aspects as using different reaction media, microwave techniques or catalyst recycling. It also provides a comprehensive treatment of modern-day coupling reactions and emphasizes those topics that show potential for future development, such as continuous flow systems, water as a reaction medium, and catalyst immobilization, among others. With its inclusion of large-scale applications, this will equally be of great interest to industrial chemists. , Kindle Edition, Ausgabe: 2, Format: Kindle eBook, Label: Wiley-VCH, Wiley-VCH, Produktgruppe: eBooks, Publiziert: 2013-02-14, Freigegeben: 2013-02-14, Studio: Wiley-VCH.

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