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Contents 1. Introduction 1 1.1. Catalysts 3 1.2. Mechanistic Aspects 4 2. Suzuki Reactions 5 2.1. Pd on Carbon (Pd/C) 5 2.1.1. In the Presence of Phosphine Ligands 5 2.1.2. In the Absence of Phosphine Ligands 6 2.1.3. Ligand-Free Suzuki Coupling in Aqueous Surfactants 8 2.1.4. Ligand-Free Suzuki Coupling under Microwave or Ultrasound Conditions 8 2.2. Palladium on Metal Oxides 9 2.2.1. Palladium-Doped KF/Al2O3 9 2.2.2. Iron Oxide Nanoparticle-Supported Pd-N-Heterocyclic Carbene Complexes 10 2.2.3. Palladium-Containing Perovskites 11 2.2.4. Miscellaneous Metal Oxides 11 2.3. Pd on Porous Aluminosilicates 11 2.4. Pd on Modified Silica 12 2.5. Pd on Clays and Other Inorganic Materials 13 3. Heck Reactions 14 3.1. Pd on Carbon (Pd/C) 14 3.2. Pd on Metal Oxides 17 3.3. Pd on Microporous and Mesoporous Supports 18 3.4. Pd on Modified Silica (Organic-Inorganic Hybrid Support) 19 3.5. Pd on Clay and Other Inorganic Materials 21 4. Sonogashira Reactions 22 4.1. Pd on Carbon (Pd/C) 22 4.1.1. In Anhydrous Media 22 4.1.2. In Organic Solvent/Water Mixtures 23 4.1.3. Copper-Free and Ligand-Free Sonogashira Coupling 25 4.2. Pd on Metal Oxides 26 4.3. Pd on Microporous and Mesoporous Supports 26 4.4. Pd on Modified Silica 27 4.5. Pd on Clay and Other Inorganic Materials 27 5. Stille, Fukuyama, and Negishi Reactions 27 5.1. Stille Reactions 27 5.1.1. Pd on Carbon (Pd/C) 27 5.1.2. Palladium on KF/Al2O3 27 5.1.3. Pd on Modified Silica (SiO2/TEG/Pd) 27 5.2. Fukuyama Reactions 27 5.2.1. Pd on Carbon (Pd/C) 27 5.2.2. Pd(OH)2 on Carbon (Perlman¡¯s Catalyst) 28 5.3. Pd/C-Catalyzed Negishi Reactions 28 6. Ullmann-Type Coupling Reactions 29 6.1. Pd/C-Catalyzed Aryl-Aryl Coupling 29 6.2. Pd/C-Catalyzed Homocoupling of Vinyl Halides 30 6.3. Pd/C-Catalyzed Intramolecular Coupling of Aryl and Vinyl Halides 30 7. Homocoupling of Arylboronic Acids, Pyridines, and Alkynes 30 7.1. Pd/C-Catalyzed Homocoupling of Arylboronic Acids (Suzuki-Type Homocoupling) 30 7.2. Pd/C-Catalyzed Homocoupling of Pyridines 30 7.3. Pd/C-Catalyzed Homocoupling of Alkynes (Glaser-Type Coupling) 32 8. Other Coupling Reactions 32 8.1. Cyanation of Aryl Bromides 32 8.2. Carbonylations 32 8.3. R-Arylations of Diethyl Malonate 33 8.4. Arylations of Aromatic Compounds 33 8.5. Allylations 34 8.6. Intermolecular Heck-Type Coupling 34 9. Pd on Solid Support in Tandem Reactions 35 9.1. Sonogashira Coupling in Tandem Reactions 35 9.2. Heck Coupling in Tandem Reactions 36 10. Conclusions and Perspectives 37 11. Abbreviations 38 12. Acknowledgments 38 13. References ²»ÖªµÀÔõô°ÑPDFÎļþ·Ö³ÉÁ½¸öÎļþ´«µÝŶ£¬µ¥¸öÌ«´óÁË |
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