Maurizio Benaglia is Associate Professor at the Department of Organic and Industrial Chemistry, University of Milan, Italy. He is author of over ninety publications in international scientific journals, including five review articles. His current research focuses on stereoselective reactions, synthesis of chiral supramolecular systems, synthesis of supported organometallic and metal-free catalysts, and design and synthesis of new chiral catalysts, and environmentally pure catalysts.

• Preface xiiiAcknowledgements xvContributors xvii1 The Experimental Assay of Catalyst Recovery: General Concepts 1John A. Gladysz1.1 Introduction 11.2 Catalyst Precursor vs Catalyst 21.3 Catalyst vs Catalyst Resting State 31.4 Catalyst Inventory: Loss Mechanisms 51.5 Evaluation of Catalyst Recovery 81.6 Prospective 132 Surface-functionalized Nanoporous Catalysts for Renewable Chemistry 15Brian G. Trewyn, Hung-Ting Chen and Victor S.-Y. Lin2.1 Introduction 152.2 Immobilization Strategies of Heterogeneous Catalysts 172.3 Efficient Heterogeneous Catalysts with Enhanced Reactivity and Selectivity with Functionality 262.4 Other Heterogeneous Catalyst Systems on Nonsilica Supports 442.5 Conclusion 453 Insoluble Resin-supported Catalysts 49Gang Zhao and Zhuo Chai3.1 Introduction 493.2 Transition Metal catalyzed c c Bond Formation Reactions 503.3 Oxidation 563.4 Reduction 613.5 Organocatalyzed Reactions 623.6 Annulation Reactions 663.7 Miscellaneous 703.8 Conclusion 724 Catalysts Bound to Soluble Polymers 77Tamilselvi Chinnusamy, Petra Hilgers and Oliver Reiser4.1 Introduction 774.2 Soluble Supports – General Considerations 784.3 Recent Developments of Soluble Polymer-supported Catalysts 794.4 Recent Examples for Reactions Promoted by Catalysts Bound to Soluble Polymers 814.5 Conclusion 985 Polymeric, Recoverable Catalytic Systems 101Qiao-Sheng Hu5.1 Introduction 1015.2 Polymeric Catalyst Systems 1025.3 Summary 1146 Thermomorphic Catalysts 117David E. Bergbreiter6.1 Introduction 1176.2 Thermomorphic Catalyst Separation Strategies 1186.3 Hydrogenation Reactions Under Thermomorphic Conditions 1226.4 Hydroformylation Reactions Under Thermomorphic Conditions 1266.5 Hydroaminations Under Thermomorphic Conditions 1296.6 Pd-catalyzed Reactions Under Thermomorphic Conditions 1306.7 Polymerization Reactions Under Thermomorphic Conditions 1386.8 Organocatalysis Under Thermomorphic Conditions 1426.9 Cu(I)-catalyzed 1,3-Dipolar Cycloadditions Under Thermomorphic Conditions 1446.10 Thermomorphic Hydrosilylation Catalysts 1446.11 Thermomorphic Catalytic Oxidations 1456.12 Conclusions 1477 Self-supported Asymmetric Catalysts 155Wenbin Lin and David J. Mihalcik7.1 Introduction 1557.2 Self-supported Asymmetric Catalysts Formed by Linking Catalytically Active Subunits via Metal–Ligand Coordination 1567.3 Self-supported Asymmetric Catalysts Formed by Post-synthetic Modifications of Coordination Polymers 1637.4 Self-supported Asymmetric Catalysts Formed by Linking Multitopic Chiral Ligands with Catalytic Metal Centers 1687.5 Conclusions and Outlook 1728 Fluorous Chiral Catalyst Immobilization 179Tibor Soos8.1 Introduction 1798.2 Fluorous Chemistry and its Basic Recovery Concepts 1808.3 Application of Fluorous Chiral Catalysts 1818.4 Summary 1969 Biphasic Catalysis: Catalysis in Supercritical CO2 and in Water 199Simon L. Desset and David J. Cole-Hamilton9.1 Introduction 1999.2 Biphasic Catalysis 2009.3 Aqueous Biphasic Catalysis 2029.4 Supercritical Carbon Dioxide 2299.5 Conclusion 24610 Asymmetric Catalysis in Ionic Liquids 259Lijin Xu and Jianliang Xiao10.1 Introduction 25910.2 Metal-catalyzed Asymmetric Reactions in ILs 26110.3 Asymmetric Organocatalytic Reactions in ILs 28710.4 Concluding Remarks 29411 Recoverable Organic Catalysts 301Maurizio Benaglia11.1 Introduction 30111.2 Achiral Organic Catalysts 30411.3 Chiral Organic Catalysts 31111.4 Catalysts Derived from Amino Acids 31911.5 General Considerations on Recyclable Organocatalysts 33411.6 Outlook and Perspectives 33612 Organic Polymer-microencapsulated Metal Catalysts 341Jun Ou and Patrick H. Toy12.1 Introduction 34112.2 Non-cross-linked Polymer-microencapsulated Catalysts 34212.3 Cross-linked Polymer-microencapsulated Catalysts 35512.4 Summary Table 37412.5 Conclusions 37513 Organic Synthesis with Mini Flow Reactors Using Immobilised Catalysts 379Sascha Ceylan and Andreas Kirschning13.1 Introduction 37913.2 Catalysis in Mini Flow Reactors with Immobilised Catalysts 38213.3 Miscellaneous Enabling Techniques for Mini Flow Systems 40413.4 Perspectives and Outlook 40614 Homogeneous Catalysis Using Microreactor Technology 411Johan C. Brandt and Thomas Wirth14.1 Introduction 41114.2 Acid-catalysed Reactions 41114.3 Liquid–liquid Biphasic Systems 41314.4 Photocatalysis 41814.5 Asymmetric Catalytic Reactions 42114.6 Unusual Reaction Conditions 42115 Catalyst Immobilization Strategy: Some General Considerations and a Comparison of the Main Features of Different Supports 427Franco Cozzi15.1 Introduction 42715.2 General Considerations on Catalyst Immobilization 42815.3 Comparison of Different Supports Employed for the Immobilization of Proline 44215.4 Comparison of Different Supports Employed for the Immobilization of Bis(oxazolines) 45215.5 Conclusions 458References 458Index 463

"This book is most appropriate for researchers or graduate students who are familiar with the area of asymmetric catalysis and seek to become more involved in this important area of research." (The Quarterly Review of Biology, 1 March 2011)"A substantial resource for those who do process development and scale-up work." (Organic Chemistry Portal, March 2010)

Maurizio Benaglia is Associate Professor at the Department of Organic and Industrial Chemistry, University of Milan, Italy. He is author of over ninety publications in international scientific journals, including five review articles. His current research focuses on stereoselective reactions, synthesis of chiral supramolecular systems, synthesis of supported organometallic and metal-free catalysts, and design and synthesis of new chiral catalysts, and environmentally pure catalysts.

• Preface xiiiAcknowledgements xvContributors xvii1 The Experimental Assay of Catalyst Recovery: General Concepts 1John A. Gladysz1.1 Introduction 11.2 Catalyst Precursor vs Catalyst 21.3 Catalyst vs Catalyst Resting State 31.4 Catalyst Inventory: Loss Mechanisms 51.5 Evaluation of Catalyst Recovery 81.6 Prospective 132 Surface-functionalized Nanoporous Catalysts for Renewable Chemistry 15Brian G. Trewyn, Hung-Ting Chen and Victor S.-Y. Lin2.1 Introduction 152.2 Immobilization Strategies of Heterogeneous Catalysts 172.3 Efficient Heterogeneous Catalysts with Enhanced Reactivity and Selectivity with Functionality 262.4 Other Heterogeneous Catalyst Systems on Nonsilica Supports 442.5 Conclusion 453 Insoluble Resin-supported Catalysts 49Gang Zhao and Zhuo Chai3.1 Introduction 493.2 Transition Metal catalyzed c c Bond Formation Reactions 503.3 Oxidation 563.4 Reduction 613.5 Organocatalyzed Reactions 623.6 Annulation Reactions 663.7 Miscellaneous 703.8 Conclusion 724 Catalysts Bound to Soluble Polymers 77Tamilselvi Chinnusamy, Petra Hilgers and Oliver Reiser4.1 Introduction 774.2 Soluble Supports – General Considerations 784.3 Recent Developments of Soluble Polymer-supported Catalysts 794.4 Recent Examples for Reactions Promoted by Catalysts Bound to Soluble Polymers 814.5 Conclusion 985 Polymeric, Recoverable Catalytic Systems 101Qiao-Sheng Hu5.1 Introduction 1015.2 Polymeric Catalyst Systems 1025.3 Summary 1146 Thermomorphic Catalysts 117David E. Bergbreiter6.1 Introduction 1176.2 Thermomorphic Catalyst Separation Strategies 1186.3 Hydrogenation Reactions Under Thermomorphic Conditions 1226.4 Hydroformylation Reactions Under Thermomorphic Conditions 1266.5 Hydroaminations Under Thermomorphic Conditions 1296.6 Pd-catalyzed Reactions Under Thermomorphic Conditions 1306.7 Polymerization Reactions Under Thermomorphic Conditions 1386.8 Organocatalysis Under Thermomorphic Conditions 1426.9 Cu(I)-catalyzed 1,3-Dipolar Cycloadditions Under Thermomorphic Conditions 1446.10 Thermomorphic Hydrosilylation Catalysts 1446.11 Thermomorphic Catalytic Oxidations 1456.12 Conclusions 1477 Self-supported Asymmetric Catalysts 155Wenbin Lin and David J. Mihalcik7.1 Introduction 1557.2 Self-supported Asymmetric Catalysts Formed by Linking Catalytically Active Subunits via Metal–Ligand Coordination 1567.3 Self-supported Asymmetric Catalysts Formed by Post-synthetic Modifications of Coordination Polymers 1637.4 Self-supported Asymmetric Catalysts Formed by Linking Multitopic Chiral Ligands with Catalytic Metal Centers 1687.5 Conclusions and Outlook 1728 Fluorous Chiral Catalyst Immobilization 179Tibor Soos8.1 Introduction 1798.2 Fluorous Chemistry and its Basic Recovery Concepts 1808.3 Application of Fluorous Chiral Catalysts 1818.4 Summary 1969 Biphasic Catalysis: Catalysis in Supercritical CO2 and in Water 199Simon L. Desset and David J. Cole-Hamilton9.1 Introduction 1999.2 Biphasic Catalysis 2009.3 Aqueous Biphasic Catalysis 2029.4 Supercritical Carbon Dioxide 2299.5 Conclusion 24610 Asymmetric Catalysis in Ionic Liquids 259Lijin Xu and Jianliang Xiao10.1 Introduction 25910.2 Metal-catalyzed Asymmetric Reactions in ILs 26110.3 Asymmetric Organocatalytic Reactions in ILs 28710.4 Concluding Remarks 29411 Recoverable Organic Catalysts 301Maurizio Benaglia11.1 Introduction 30111.2 Achiral Organic Catalysts 30411.3 Chiral Organic Catalysts 31111.4 Catalysts Derived from Amino Acids 31911.5 General Considerations on Recyclable Organocatalysts 33411.6 Outlook and Perspectives 33612 Organic Polymer-microencapsulated Metal Catalysts 341Jun Ou and Patrick H. Toy12.1 Introduction 34112.2 Non-cross-linked Polymer-microencapsulated Catalysts 34212.3 Cross-linked Polymer-microencapsulated Catalysts 35512.4 Summary Table 37412.5 Conclusions 37513 Organic Synthesis with Mini Flow Reactors Using Immobilised Catalysts 379Sascha Ceylan and Andreas Kirschning13.1 Introduction 37913.2 Catalysis in Mini Flow Reactors with Immobilised Catalysts 38213.3 Miscellaneous Enabling Techniques for Mini Flow Systems 40413.4 Perspectives and Outlook 40614 Homogeneous Catalysis Using Microreactor Technology 411Johan C. Brandt and Thomas Wirth14.1 Introduction 41114.2 Acid-catalysed Reactions 41114.3 Liquid–liquid Biphasic Systems 41314.4 Photocatalysis 41814.5 Asymmetric Catalytic Reactions 42114.6 Unusual Reaction Conditions 42115 Catalyst Immobilization Strategy: Some General Considerations and a Comparison of the Main Features of Different Supports 427Franco Cozzi15.1 Introduction 42715.2 General Considerations on Catalyst Immobilization 42815.3 Comparison of Different Supports Employed for the Immobilization of Proline 44215.4 Comparison of Different Supports Employed for the Immobilization of Bis(oxazolines) 45215.5 Conclusions 458References 458Index 463

"This book is most appropriate for researchers or graduate students who are familiar with the area of asymmetric catalysis and seek to become more involved in this important area of research." (The Quarterly Review of Biology, 1 March 2011)"A substantial resource for those who do process development and scale-up work." (Organic Chemistry Portal, March 2010)

Maurizio Benaglia is Associate Professor at the Department of Organic and Industrial Chemistry, University of Milan, Italy. He is author of over ninety publications in international scientific journals, including five review articles. His current research focuses on stereoselective reactions, synthesis of chiral supramolecular systems, synthesis of supported organometallic and metal-free catalysts, and design and synthesis of new chiral catalysts, and environmentally pure catalysts.

• Preface xiiiAcknowledgements xvContributors xvii1 The Experimental Assay of Catalyst Recovery: General Concepts 1John A. Gladysz1.1 Introduction 11.2 Catalyst Precursor vs Catalyst 21.3 Catalyst vs Catalyst Resting State 31.4 Catalyst Inventory: Loss Mechanisms 51.5 Evaluation of Catalyst Recovery 81.6 Prospective 132 Surface-functionalized Nanoporous Catalysts for Renewable Chemistry 15Brian G. Trewyn, Hung-Ting Chen and Victor S.-Y. Lin2.1 Introduction 152.2 Immobilization Strategies of Heterogeneous Catalysts 172.3 Efficient Heterogeneous Catalysts with Enhanced Reactivity and Selectivity with Functionality 262.4 Other Heterogeneous Catalyst Systems on Nonsilica Supports 442.5 Conclusion 453 Insoluble Resin-supported Catalysts 49Gang Zhao and Zhuo Chai3.1 Introduction 493.2 Transition Metal catalyzed c c Bond Formation Reactions 503.3 Oxidation 563.4 Reduction 613.5 Organocatalyzed Reactions 623.6 Annulation Reactions 663.7 Miscellaneous 703.8 Conclusion 724 Catalysts Bound to Soluble Polymers 77Tamilselvi Chinnusamy, Petra Hilgers and Oliver Reiser4.1 Introduction 774.2 Soluble Supports – General Considerations 784.3 Recent Developments of Soluble Polymer-supported Catalysts 794.4 Recent Examples for Reactions Promoted by Catalysts Bound to Soluble Polymers 814.5 Conclusion 985 Polymeric, Recoverable Catalytic Systems 101Qiao-Sheng Hu5.1 Introduction 1015.2 Polymeric Catalyst Systems 1025.3 Summary 1146 Thermomorphic Catalysts 117David E. Bergbreiter6.1 Introduction 1176.2 Thermomorphic Catalyst Separation Strategies 1186.3 Hydrogenation Reactions Under Thermomorphic Conditions 1226.4 Hydroformylation Reactions Under Thermomorphic Conditions 1266.5 Hydroaminations Under Thermomorphic Conditions 1296.6 Pd-catalyzed Reactions Under Thermomorphic Conditions 1306.7 Polymerization Reactions Under Thermomorphic Conditions 1386.8 Organocatalysis Under Thermomorphic Conditions 1426.9 Cu(I)-catalyzed 1,3-Dipolar Cycloadditions Under Thermomorphic Conditions 1446.10 Thermomorphic Hydrosilylation Catalysts 1446.11 Thermomorphic Catalytic Oxidations 1456.12 Conclusions 1477 Self-supported Asymmetric Catalysts 155Wenbin Lin and David J. Mihalcik7.1 Introduction 1557.2 Self-supported Asymmetric Catalysts Formed by Linking Catalytically Active Subunits via Metal–Ligand Coordination 1567.3 Self-supported Asymmetric Catalysts Formed by Post-synthetic Modifications of Coordination Polymers 1637.4 Self-supported Asymmetric Catalysts Formed by Linking Multitopic Chiral Ligands with Catalytic Metal Centers 1687.5 Conclusions and Outlook 1728 Fluorous Chiral Catalyst Immobilization 179Tibor Soos8.1 Introduction 1798.2 Fluorous Chemistry and its Basic Recovery Concepts 1808.3 Application of Fluorous Chiral Catalysts 1818.4 Summary 1969 Biphasic Catalysis: Catalysis in Supercritical CO2 and in Water 199Simon L. Desset and David J. Cole-Hamilton9.1 Introduction 1999.2 Biphasic Catalysis 2009.3 Aqueous Biphasic Catalysis 2029.4 Supercritical Carbon Dioxide 2299.5 Conclusion 24610 Asymmetric Catalysis in Ionic Liquids 259Lijin Xu and Jianliang Xiao10.1 Introduction 25910.2 Metal-catalyzed Asymmetric Reactions in ILs 26110.3 Asymmetric Organocatalytic Reactions in ILs 28710.4 Concluding Remarks 29411 Recoverable Organic Catalysts 301Maurizio Benaglia11.1 Introduction 30111.2 Achiral Organic Catalysts 30411.3 Chiral Organic Catalysts 31111.4 Catalysts Derived from Amino Acids 31911.5 General Considerations on Recyclable Organocatalysts 33411.6 Outlook and Perspectives 33612 Organic Polymer-microencapsulated Metal Catalysts 341Jun Ou and Patrick H. Toy12.1 Introduction 34112.2 Non-cross-linked Polymer-microencapsulated Catalysts 34212.3 Cross-linked Polymer-microencapsulated Catalysts 35512.4 Summary Table 37412.5 Conclusions 37513 Organic Synthesis with Mini Flow Reactors Using Immobilised Catalysts 379Sascha Ceylan and Andreas Kirschning13.1 Introduction 37913.2 Catalysis in Mini Flow Reactors with Immobilised Catalysts 38213.3 Miscellaneous Enabling Techniques for Mini Flow Systems 40413.4 Perspectives and Outlook 40614 Homogeneous Catalysis Using Microreactor Technology 411Johan C. Brandt and Thomas Wirth14.1 Introduction 41114.2 Acid-catalysed Reactions 41114.3 Liquid–liquid Biphasic Systems 41314.4 Photocatalysis 41814.5 Asymmetric Catalytic Reactions 42114.6 Unusual Reaction Conditions 42115 Catalyst Immobilization Strategy: Some General Considerations and a Comparison of the Main Features of Different Supports 427Franco Cozzi15.1 Introduction 42715.2 General Considerations on Catalyst Immobilization 42815.3 Comparison of Different Supports Employed for the Immobilization of Proline 44215.4 Comparison of Different Supports Employed for the Immobilization of Bis(oxazolines) 45215.5 Conclusions 458References 458Index 463

"This book is most appropriate for researchers or graduate students who are familiar with the area of asymmetric catalysis and seek to become more involved in this important area of research." (The Quarterly Review of Biology, 1 March 2011)"A substantial resource for those who do process development and scale-up work." (Organic Chemistry Portal, March 2010)