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Catalysis in Ionic Liquids
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Contents 1. Introduction 2 2. Nanostabilized Catalysts in ILs 3 2.1. ILs as Solvents for Synthesis of Nanoparticles 3 2.2. Active Complexes of Metal Compounds with ILs 5 2.3. Supported IL-Stabilized Catalysts 5 2.4. ILs as Templates for Heterogeneous Catalysts 7 2.5. Stabilization of IL Emulsions by Nanoparticles 9 3. Hydrogenations in ILs 9 3.1. Hydrogenation on IL-Stabilized Nanoparticles 9 3.1.1. Hydrogenation of 1,3-Butadiene 9 3.1.2. Hydrogenation of Alkenes and Arenes 10 3.1.3. Hydrogenation of Ketones 10 3.2. Homogeneous Catalytic Hydrogenation in ILs 10 3.3. Hydrogenation of Functionalized ILs 11 3.3.1. Selective Hydrogenation of Polymers 11 3.4. Asymmetric Hydrogenations 12 3.4.1. Enantioselective Hydrogenation 12 3.5. Role of the ILs Purity in Hydrogenation Reactions 14 3.6. Hydrogenation via Heterogeneous Catalysis in ILs 14 3.7. Biocatalysis in ILs for Reduction of Organic Molecules 16 3.8. Hydrogen-Transfer Reactions in ILs 16 4. Catalytic Oxidation in ILs 17 4.1. ILs as a Media for Organic Oxidations 17 4.2. Homogeneous Catalytic Oxidation in ILs 18 4.2.1. Glaser Oxidative Coupling 18 4.2.2. Epoxidation 18 4.2.3. Hydrocarbons to Other Oxygenated Compounds 18 4.2.4. Alcohols to Carbonyl and Carbonyl to Carboxylate Compounds 19 4.2.5. Oxidation of CdNOH Bonds 20 4.2.6. Oxidation of Thiols 20 4.2.7. Oxybromination 21 4.3. Homogeneous Asymmetric Catalytic Oxidation in ILs 21 4.4. ILs in Kinetic Resolution Reactions 21 4.5. Heterogeneous Catalytic Oxidation in ILs 21 4.6. Electrochemical Oxidation in ILs 22 4.7. Biooxidation in ILs 23 5. Acid-Base-Catalyzed Reactions in ILs 24 5.1. Acid-Catalyzed C-C and C-X Bond-Forming Reactions 24 5.1.1. Sakurai Reaction 25 5.1.2. Henry Reaction 25 5.1.3. Carbonyl Allylation of Aldehydes and Ketones 25 5.1.4. Stille Coupling 25 5.2. Sulfonylation Reactions of Aromatics 25 5.3. Silylstannations of R,‚-Unsaturated Carbonyl Compounds 26 5.4. Debromination of 2-Bromoketones 26 5.5. Protection of Carbonyls to Acetals and Ketals 26 5.6. Deprotection 26 5.7. Ligand Substitution Reactions: Fluorination Reactions 26 5.8. Isomerization 27 5.9. Acid-Catalyzed Reactions in ILs Using Heterogeneous Catalysts 27 5.10. Deoximation 27 5.11. Acid-Catalyzed Reactions with Task-Specific ILs 28 5.12. Base-Catalyzed Reactions 28 5.13. Enzymatic Catalyzed Aldol Reactions in ILs 29 6. Carbonylation and Hydroformylation 29 6.1. Carbonylation 29 6.1.1. Carbonylation of Aromatic Hydrocarbons via Homogeneous Catalysis 29 6.1.2. Carbonylation of Aryl Halides and Terminal Alkynes via Homogeneous Catalysis 29 6.1.3. Pauson-Khand Reaction 30 6.1.4. Carbonylation of Alcohols via Homogeneous Catalysis 30 6.1.5. Carbonylation of Amines and Nitrobenzene via Homogeneous Catalysis 30 6.2. Carbonylation via Heterogeneous Catalysis 31 6.2.1. Carbonylation of Amines and Nitrobenzene 31 6.3. Hydroformylation 31 6.4. Hydroformylation via Heterogeneous Catalysis 32 7. Dimerization 32 7.1. Diels-Alder Reactions 34 8. Polymerization 34 8.1. Radical Polymerization in ILs 35 8.2. Charge-Transfer Polymerization 35 8.3. Radical Polymerization Using Chiral ILs and/or Chiral Ligands 8.4. Biphasic Radical Polymerization 36 8.5. Ionic Polymerization 36 8.6. Oxidative Polymerization 36 9. Heck Reaction 36 9.1. Homogeneous Catalysis 36 9.2. Heterogeneous Catalysis 38 10. Suzuki Cross-Coupling 39 10.1. Heterogeneous Catalysis 39 11. Other Reactions 39 11.1. Hydroarylation 39 11.2. Hydroesterification 39 11.3. Ring-Closing Metathesis of Di-, Tri-, and Tetrasubstituted Dienes 40 11.4. Trost-Tsuji C-C Coupling 40 11.5. Thioacetalization of Carbonyl Compounds 40 11.6. Gewald Synthesis 41 11.7. Reactions of Carbonyl Compounds 41 11.7.1. Reactions with Indoles 41 11.7.2. Michael Additions 41 11.7.3. Baylis-Hillman Reaction 43 11.7.4. Stetter Reaction 43 11.7.5. Cross-Coupling between Aldehydes and Allylic Alcohols 43 11.7.6. Cross-Condensation of Carbonyl Compounds with Derivatives of Cyanoacetic Acid 43 11.7.7. Mannich-type Reaction 43 11.7.8. Mukaiyama Aldol Reaction 44 11.7.9. Reductive Amination of Carbonyl Compounds with Amines 44 11.7.10.1,4-Conjugate Addition of Unmodified Aldehyde 44 11.7.11.Carbonyl-Ene Reaction 44 11.7.12.Tandem Cyclization-1,3-Dipolar Cycloaddition Reaction of R-Diazo Ketones 44 11.7.13.CO2 Cycloaddition to Epoxide 45 11.7.14.R-Tosyloxylation of Ketones 45 11.8. Heterogeneous Catalysis 45 11.8.1. Hydroamination Reactions 45 12. Conclusions 45 13. Acknowledgment 46 14. References 46 [ Last edited by daiqiguang on 2007-6-3 at 11:26 ] |
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