Table of Contents XIX. Introduction J. G. de Vries. Introduction X. Tan, H. Lv, and X. Zhang

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1 XIX Introduction J. G. de Vries Introduction Reduction of Alkenes Homogeneous Reduction of Alkenes X. Tan, H. Lv, and X. Zhang Homogeneous Reduction of Alkenes Reduction of Nonfunctionalized Alkenes Reduction of Nitrogen-Substituted Alkenes Reduction of Enamides Reduction of Æ,â-Dehydro-Æ-amino Acids and Their Esters Reduction of Æ,â-Dehydro-â-amino Acids and Their Esters Reduction of Oxygen-Substituted Alkenes Reduction of Enol Esters Reduction of Enol Phosphinates Reduction of Enol Ethers Reduction of Silyl Enol Ethers Reduction of Carbonyl-Substituted Alkenes Reduction of Æ,â-Unsaturated Carboxylic Acids Reduction of Æ,â-Unsaturated Esters Reduction of Æ,â-Unsaturated Amides Reduction of Æ,â-Unsaturated Ketones Reduction of Alkenes Bearing Other Heteroatoms Reduction of Phosphorus-Substituted Alkenes Reduction of Vinylboronates Reduction of Vinyl Fluorides Reduction of Sulfur-Substituted Alkenes... 59

2 XX Reduction of Alkenes Using Nanoparticle Catalysis R. Hudson and A. Moores Reduction of Alkenes Using Nanoparticle Catalysis Reduction of Alkenes by Hydrogenation Using Palladium Nanoparticles Hydrogenation with Commercial Palladium Nanoparticles Hydrogenation with Palladium Nanoparticles in Poly(ethylene glycol) Hydrogenation with Palladium Nanoparticles Stabilized in Mesocellular Foam Hydrogenation with Phenanthroline-Stabilized Palladium Nanoparticles in Poly(ethylene glycol) Hydrogenation with Palladium Nanoparticles Embedded in Polystyrene Hydrogenation with Palladium Nanoparticles on Amphiphilic Supports Hydrogenation with Palladium Nanoparticles in Biphasic Media Asymmetric Hydrogenation with Palladium Nanoparticles Hydrogenation with Palladium on Ferrite Nanoparticles Hydrogenation with Palladium Nanoparticles Supported on Magnetic Carbon-Coated Cobalt Nanobeads Hydrogenation with Magnetic Carbon-Supported Palladium Nanoparticles Reduction of Alkenes by Hydrogenation Using Iron Nanoparticles Hydrogenation with Unsupported Iron Nanoparticles Hydrogenation with Graphene-Supported Iron Nanoparticles Hydrogenation with Core-Shell Iron/Iron Oxide Nanoparticles Hydrogenation with Amphiphilic Polymer-Supported Iron Nanoparticles Reduction of Alkenes Using Ionic-Liquid-Stabilized Nanoparticles Reduction of Alkenes with Iridium Nanoparticles in Ionic Liquids Reduction of Alkenes by Transfer Hydrogenation Selective Reduction of Alkenes with Hydrazine Using Nickel Nanoparticles Supported on Clay Selective Reduction of Alkenes with Isopropanol Using Nickel Nanoparticles Selective Reduction of Alkenes with Isopropanol Catalyzed by Nickel/Ruthenium/Platinum/Gold Heteroquatermetallic Nanoparticles Conclusions and Future Perspectives... 88

3 XXI 1.2 Partial Reduction of Polyenes F. Zaccheria and N. Ravasio 1.2 Partial Reduction of Polyenes Selective Hydrogenation of Polyunsaturated Terpenes Isoprene Reduction Limonene Reduction Myrcene Reduction Geraniol Reduction Homogeneous Catalysts for Geraniol Reduction Heterogeneous Catalysts for Geraniol Reduction Partial Hydrogenation of Cyclic Polyenes Cyclooctadiene Reduction Cyclododecatriene Reduction Selective Hydrogenation of Vegetable Oils and Related Compounds Two-Phase Systems Homogeneous Systems Noble Metal Based Heterogeneous Systems Non-Noble Metal Based Heterogeneous Systems Conclusions Reduction of Arenes X. Dai and F. Shi 1.3 Reduction of Arenes Reduction of Monocyclic Arenes to Cycloalkanes Ruthenium-Catalyzed Reduction of Monocyclic Arenes to Cycloalkanes Rhodium-Catalyzed Reduction of Monocyclic Arenes to Cycloalkanes Iridium-Catalyzed Reduction of Monocyclic Arenes to Cycloalkanes Palladium-Catalyzed Reduction of Monocyclic Arenes to Cycloalkanes Reduction of Polycyclic Arenes Ruthenium-Catalyzed Reduction of Polycyclic Arenes Rhodium-Catalyzed Reduction of Polycyclic Arenes Platinum-Catalyzed Reduction of Polycyclic Arenes Palladium-Catalyzed Reduction of Polycyclic Arenes Borane-Catalyzed Reduction of Polycyclic Arenes Reduction of Polycyclic Arenes Catalyzed by Lewis Pairs

4 XXII Reduction of Monocyclic Arenes to Cycloalkenes Ruthenium-Catalyzed Reduction of Monocyclic Arenes to Cycloalkenes Rhodium-Catalyzed Reduction of Monocyclic Arenes to Cycloalkenes Reduction of Hetarenes Z.-P. Chen and Y.-G. Zhou 1.4 Reduction of Hetarenes Heterogeneous Catalysis Reduction of Quinoline Derivatives Reduction of Isoquinoline Derivatives Reduction of Pyridine Derivatives Homogeneous Catalysis Racemic Reductions Reduction of Quinoline Derivatives Miscellaneous Substrates Enantioselective Reductions Neutral Iridium Complexes as Catalysts Cationic Iridium Complexes as Catalysts Ruthenium Complexes as Catalysts Rhodium Complexes as Catalysts Palladium Complexes as Catalysts Conclusions and Future Perspectives Catalytic Reduction of Alkynes and Allenes W. Bonrath, J. A. Medlock, and M.-A. Müller 1.5 Catalytic Reduction of Alkynes and Allenes Reduction of Alkynes Total Hydrogenation of Alkynes to Alkanes Selective Hydrogenation of Alkynes to Alkenes Semi-hydrogenations of Terminal Alkynes and Z-Selective Reduction of Internal Alkynes Heterogeneous Hydrogenations Heterogeneous Transfer Hydrogenations Homogeneous Hydrogenations Homogeneous Transfer Hydrogenations

5 XXIII E-Selective Semi-hydrogenations of Internal Alkynes Homogeneous Hydrogenations Homogeneous Transfer Hydrogenations Reduction of Allenes Hydrogenation of Functionalized Allenes Hydrogenation of Allene Ketones Conclusions Catalytic Reduction of Phenols, Alcohols, and Diols S. Tin and J. G. de Vries 1.6 Catalytic Reduction of Phenols, Alcohols, and Diols Hydrodeoxygenation of Phenols To Give Arenes Hydrodeoxygenation of Aliphatic Alcohols To Give Alkanes Reduction of Diols To Give Alkenes Reduction of Diols by Metal-Free Catalysis Reduction of Diols Using Rhenium Catalysts Conclusions Hydrogenolysis of Ethers Y. Nakagawa, M. Tamura, and K. Tomishige 1.7 Hydrogenolysis of Ethers Hydrogenolysis of Aryl Ethers Homogeneous Nickel Catalysts for the Hydrogenolysis of Diaryl Ethers and Alkyl Aryl Ethers Solid Catalysts for the Hydrogenolysis of Aryl Ethers Hydrogenolysis of the â-o-4 Linkage in Lignin Model Compounds Hydrogenolysis of Methoxy Groups in Lignin Model Monomers Hydrogenolysis of Saturated Ethers Ethers Bearing Directing Hydroxy Groups Ethers without Directing Hydroxy Groups Total Hydrodeoxygenation of Cyclic Ethers to Alkanes Hydrogenolysis of Furans Hydrogenolysis via Tetrahydrofuran Derivatives Ring Opening of Furan Derivatives not Involving a Tetrahydrofuran Intermediate Conclusions

6 XXIV 1.8 Catalytic Reduction of Carbonates Y. Li and K. Ding 1.8 Catalytic Reduction of Carbonates Catalytic Reduction of Carbonates to Formates Homogeneous Reductions Heterogeneous Reductions Catalytic Reduction of Dialkyl Carbonates to Methanol Homogeneous Reductions Heterogeneous Reductions Catalytic Reduction of Carbonates to Methane Other Reductive Transformations Catalytic Reductive Methylation Photo-/Electro- and Enzymatic Reduction of Carbonates Conclusions Hydrogenation of Carbon Dioxide F. Nahra and C. S. J. Cazin 1.9 Hydrogenation of Carbon Dioxide Hydrogenation of Carbon Dioxide to Formic Acid or Formate Salts Homogeneous Systems Rhodium-Based Catalysts Ruthenium-Based Catalysts Iridium-Based Catalysts Other Metal-Based Catalysts Heterogeneous Systems Hydrogenation of Carbon Dioxide to Methanol Homogeneous Systems Heterogeneous Systems Methanation of Carbon Dioxide Heterogeneous Systems Reductive Methylation Using Carbon Dioxide Methylation of Amines Homogeneous Systems Methylation of Amines Using Hydrogen as Reductant Heterogeneous Systems Methylation of C-H Bonds

7 XXV 1.10 Reduction of Peroxo Compounds, Ozonides, and Molozonides P. Poechlauer and A. Zimmermann 1.10 Reduction of Peroxo Compounds, Ozonides, and Molozonides Reduction of Peroxo Compounds Mechanistic Aspects and New Types of Catalysts Reduction of Peroxo Compounds in the Presence of Other Reducible Functional Groups Reduction of Peroxo Compounds in the Presence of Alkenes, Esters, Lactones, and Lactams Reduction of Peroxo Compounds in the Presence of Oxo Groups Hydrogenation of Æ-Peroxy Carbonyl Compounds Hydrogenation of â-peroxy Carbonyl Compounds Hydrogenation of ª-Peroxy Carbonyl Compounds Reduction of Peroxo Compounds in the Presence of Nitro Groups Reduction of Peroxides as Part of Multistep Syntheses Hydrogenation of Hydroperoxides Formed by an Ene Reaction of Singlet Oxygen with a C=C Bond Hydrogenation of Dialkyl Peroxides Formed by Addition of an Alkyl Hydroperoxide to a C=C Bond To Effect a Net Hydration of this Double Bond Hydrogenation of 1,2-Dioxin Derivatives Formed by [2 +4] Cycloaddition of Singlet Oxygen to 1,3-Dienes To Effect 1,4-Dihydroxylation Dihydroxylation and Hydrogenation of 4-Substituted 1,2-Dioxins Hydrogenation of Endoperoxides Formed by [2 +4] Cycloaddition of Singlet Oxygen to Cyclic 1,3-Dienes To Effect cis-1,4-dihydroxylation Cyclohexanetetraols by Hydrogenation of 2,3-Dioxabicyclo[2.2.2]octane-5,6-diols Hydroxycyclohexenones by Hydrogenation of 1-Alkoxy-2,3-dioxabicyclo[2.2.2]oct-5-enes ,7-Dioxabicyclo[2.2.1]heptanes by Hydrogenation of 2,3,5-Trioxabicyclo[2.2.2]oct-7-enes Reduction of Molozonides, Ozonides, and Hydroxy and Alkoxy Hydroperoxides 331

8 XXVI 1.11 Reduction of Sulfur Compounds Using Metal Catalysts K. Kaneda and T. Mitsudome 1.11 Reduction of Sulfur Compounds Using Metal Catalysts Deoxygenation of Sulfoxides to Thioethers Using Alcohols Deoxygenation of Sulfoxides and Sulfones to Thioethers Using Molecular Hydrogen Reduction of Disulfides to Thiols Using Molecular Hydrogen Conclusions and Future Perspectives Catalytic Hydrodehalogenation Reactions B. Ghosh and R. E. Maleczka, Jr Catalytic Hydrodehalogenation Reactions Metal-Catalyzed Hydrodehalogenation Heterogeneous Catalysis Homogeneous Catalysis Photoinduced Hydrodehalogenation Conclusions Keyword Index Author Index Abbreviations