Carbon-Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium catalysts.pdfVIP

Chem. Rev. 2007, 107, 133?173 133 Carbon?Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts Lunxiang Yin and Ju¨rgen Liebscher* Institute fu¨r Chemie, Humboldt-Universita¨t Berlin, Brook-Taylor-Strasse 2, D-12489 Berlin, Germany Received January 16, 2006 Contents 5.2. Fukuyama Reactions 159 5.2.1. Pd on Carbon Pd/C 159 1. Introduction 133 5.2.2. Pd OH 2 on Carbon Perlman’s Catalyst 160 1.1. Catalysts 135 5.3. Pd/C-Catalyzed Negishi Reactions 160 1.2. Mechanistic Aspects 136 6. Ullmann-Type Coupling Reactions 161 2. Suzuki Reactions 137 6.1. Pd/C-Catalyzed Aryl?Aryl Coupling 161 2.1. Pd on Carbon Pd/C 137 6.2. Pd/C-Catalyzed Homocoupling of Vinyl 162 2.1.1. In the Presence of Phosphine Ligands 137 Halides 2.1.2. In the Absence of Phosphine Ligands 138 6.3. Pd/C-Catalyzed Intramolecular Coupling of 162 2.1.3. Ligand-Free Suzuki Coupling in Aqueous 140 Aryl and Vinyl Halides Surfactants 7. Homocoupling of Arylboronic Acids, Pyridines, 162 2.1.4. Ligand-Free Suzuki Coupling under 140 and Alkynes Microwave or Ultrasound Conditions 7.1. Pd/C-Catalyzed Homocoupling of Arylboronic 162 2.2. Palladium on Metal Oxides 141 Acids Suzuki-Type Homocoupling 2.2.1. Palladium-Doped KF/Al2O3 141 7.2. Pd/C-Catalyzed Homocoupling of Pyridines 162 2.2.2. Iron Oxide Nanoparticle-Supported 142 7.3. Pd/C-Catalyzed Homocoupling of Alkynes 164 Pd?N-Heterocyclic Carbene Complexes Glaser-Type Coupling 2.2.3. Palladium-Containing Perovskites 143 8. Other Coupling Reactions 164 2.2.4. Miscellaneous Metal Oxides 143 8.1. Cyanation of Aryl Bromides 164 2.3. Pd on Porous Aluminosilicates 143 8.2. Carbonylations 164 2.4. Pd on Modified Silica 144 8.3. -Arylations of Diethyl Malonate 165 2.5. Pd on Clays and Other Inorganic Materials 145 8.4. Arylations of Aromatic Compounds 165 3. Heck Reactions 146 8.5. Allylations 166 3.1. Pd on Carbon Pd/C 146 8.6. Intermolecular Heck-Type Coupling 166 3.2. Pd on Metal Oxides 149 9. Pd on Solid S