Foreword. Preface. List of Contributors. Part I Introduction, Organometallic Aspects and Mechanism of Homogeneous Hydrogenation. 1 Rhodium (Luis A. Oro and Daniel Carmona). 1.1 Introduction. 1.2 The Early Years (1939-1970). 1.3 The [RhH(CO)(PPh3)3] Catalyst. 1.4 The [RhCl(PPh3)3] Complex and Related Catalysts. 1.5 The Cationic[Rh(diene)(PR3)X]+ Catalysts. 1.6 Enantioselective Rhodium Catalysts. 1.7 Some Dinuclear Catalyst Precursors. 1.8 Concluding Remark. Abbreviations. References. 2 Iridium (Robert H. Crabtree). 2.1 Introduction. 2.2 Historical Aspects. 2.3 Organometallic Aspects. 2.4 Catalysis. Acknowledgments. Abbreviations. References. 3 Ruthenium and Osmium (Robert H. Morris). 3.1 Introduction. 3.2 Ruthenium. 3.3 Osmium. Acknowledgment. Abbreviations. References. 4 Palladium and Platinum (Paolo Pelagatti). 4.1 Introduction. 4.2 Palladium. 4.3 Platinum. Abbreviations. References. 5 Nickel (Elisabeth Bouwman). 5.1 Introduction. 5.2 Coordination Chemistry and Organometallic Aspects of Nickel. 5.3 Hydrogenation Catalysis. 5.4 Concluding Remarks. Abbreviations. References. 6 Hydrogenation with Early Transition Metal, Lanthanide and Actinide Complexes (Christophe Coperet). 6.1 Introduction. 6.2 Mechanistic Considerations. 6.3 Group IV Metal Hydrogenation Catalysts. 6.4 Hydrogenation Catalysts Based on Group III, Lanthanide, and Actinide Complexes. 6.5 Hydrogenation Catalysts Based on Groups V-VII Transition-Metal Complexes. 6.6 Supported Early Transition-Metal Complexes as Heterogeneous Hydrogenation Catalysts. 6.7 Conclusions. Acknowledgments. Abbreviations. References. 7 Ionic Hydrogenations (R. Morris Bullock). 7.1 Introduction. 7.2 Stoichiometric Ionic Hydrogenations. 7.3 Catalytic Ionic Hydrogenation. 7.4 Ruthenium Complexes Having an OH Proton Donor and a RuH as Hydride Donor. 7.5 Catalytic Hydrogenation of Ketones by Strong Bases. 7.6 Conclusion. Acknowledgments. Abbreviations. References. 8 Homogeneous Hydrogenation by Defined Metal Clusters (Roberto A. Sanchez-Delgado). 8.1 Introduction. 8.2 Hydrogenation of C=C Bonds. 8.3 Hydrogenation of CC Bonds. 8.4 Hydrogenation of Other Substrates. 8.5 Concluding Remarks. Abbreviations. References. 9 Homogeneous Hydrogenation: Colloids - Hydrogenation with Noble Metal Nanoparticles (Alain Roucoux and Karine Philippot ). 9.1 Introduction. 9.2 Concepts. 9.3 Hydrogenation of Compounds with C=C Bonds. 9.4 Hydrogenation of Compounds with CC Bonds. 9.5 Arene Hydrogenation. 9.6 Hydrogenation of Compounds with C=O Bonds. 9.7 Enantioselective Hydrogenation. 9.8 Conclusion. Abbreviations. References. 10 Kinetics of Homogeneous Hydrogenations: Measurement and Interpretation (Hans-Joachim Drexler, Angelika Preetz, Thomas Schmidt, and Detlef Heller). 10.1 Introduction. 10.2 The Basics of Michaelis-Menten Kinetics. 10.3 Hydrogenation From a Kinetic Viewpoint. Abbreviations. References. Part II Spectroscopic Methods in Homogeneous Hydrogenation 11 Nuclear Magnetic Resonance Spectroscopy in Homogeneous Hydrogenation Research (N. Koen de Vries). 11.1 Introduction. 11.2 NMR Methods. 11.3 Outlook. Abbreviations. References. 12 Parahydrogen-Induced Polarization: Applications to Detect Intermediates of Catalytic Hydrogenations (Joachim Bargon). 12.1 In-Situ Spectroscopy. 12.2 Ortho- and Parahydrogen. 12.3 Applications of PHIP-NMR Spectroscopy. 12.4 Catalyst-Attached Products as Observable Intermediates. 12.5 Colloidal Catalysts. 12.6 Transfer of Proton Polarization to Heteronuclei. 12.7 Catalysts Containing other Transition Metals. 12.8 Summary and Conclusions. Acknowledgment. Abbreviations. References. 13 A Tour Guide to Mass Spectrometric Studies of Hydrogenation Mechanisms (Corbin K. Ralph, Robin J. Hamilton, and Steven H. Bergens). 13.1 Introduction. 13.2 A General Description of ESI-MS. 13.3 Mechanistic Hydrogenation Studies. 13.4 Conclusions. Acknowledgments. Abbreviations. References. Part III Homogeneous Hydrogenation by Functional Groups. 14 Homogeneous Hydrogenation of Alkynes and Dienes (Alexander M. Kluwer and Cornelis J. Elsevier). 14.1 Stereoselective Homogeneous Hydrogenation of Alkynes to Alkenes. 14.2 Homogeneous Hydrogenation of Dienes to Monoenes. Abbreviations. References. 15 Homogeneous Hydrogenation of Aldehydes, Ketones, Imines and Carboxylic Acid Derivatives: Chemoselectivity and Catalytic Activity (Matthew L. Clarke and Geoffrey J. Roff). 15.1 Introduction. 15.2 Hydrogenation of Aldehydes. 15.3 Hydrogenation of Ketones. 15.4 Domino-Hydroformylation-Reduction Reactions. 15.5 Reductive Amination of Ketones and Aldehydes. 15.6 Hydroaminomethylation of Alkenes (Domino Hydroformylation-Reductive Amination). 15.7 Hydrogenation of Carboxylic Acid Derivatives. 15.8 Summary and Outlook. Abbreviations. References. 16 Hydrogenation of Arenes and Heteroaromatics (Claudio Bianchini, Andrea Meli, and Francesco Vizza). 16.1 Introduction. 16.2 Hydrogenation of Arenes. 16.3 Hydrogenation of Heteroaromatics. 16.4 Stereoselective Hydrogenation of Prochiral Heteroaromatics. Abbreviations. References. 17 Homogeneous Hydrogenation of Carbon Dioxide (Philip G. Jessop). 17.1 Introduction. 17.2 Reduction to Formic Acid. 17.3 Reduction to Oxalic Acid. 17.4 Reduction to Formate Esters. 17.5 Reduction to Formamides. 17.6 Reduction to Other Products. 17.7 Concluding Remarks. Acknowledgments. Abbreviations. References. 18 Dehalogenation Reactions (Attila Sisak and Otto Balazs Simon). 19 Homogeneous Catalytic Hydrogenation of Polymers (Garry L. Rempel, Qinmin Pan, and Jialong Wu). 20 Transfer Hydrogenation Including the Meerwein-Ponndorf-Verley Reduction (Dirk Klomp, Ulf Hanefeld, and Joop A. Peters). 21 Diastereoselective Hydrogenation (Takamichi Yamagishi). 22 Hydrogen-Mediated Carbon-Carbon Bond Formation Catalyzed by Rhodium (Chang-Woo Cho and Michael J. Krische). Part IV Asymmetric Homogeneous Hydrogenation. 23 Enantioselective Alkene Hydrogenation: Introduction and Historic Overview (David J. Ager). 24 Enantioselective Hydrogenation: Phospholane Ligands (Christopher J. Cobley and Paul H. Moran). 25 Enantioselective Hydrogenation of Alkenes with Ferrocene-Based Ligands (Hans-Ulrich Blaser, Matthias Lotz, and Felix Spindler). 26 The other Bisphosphine Ligands for Enantioselective Alkene Hydrogenation (Yongxiang Chi, Wenjun Tang, and Xumu Zhang). 27 Bidentate Ligands Containing a Heteroatom-Phosphorus Bond (Stanton H.L. Kok, Terry T.-L. Au-Yeung, Hong Yee Cheung, Wing Sze Lam, Shu Sun Chan, and Albert S. C. Chan). 28 Enantioselective Alkene Hydrogenation: Monodentate Ligands (Michel van den Berg, Ben L. Feringa, and Adriaan J. Minnaard). 29 P,N and Non-Phosphorus Ligands (Andreas Pfaltz and Sharon Bell). 30 Enantioselective Hydrogenation of Unfunctionalized Alkenes (Andreas Pfaltz and Sharon Bell). 31 Mechanism of Enantioselective Hydrogenation (John M. Brown). 32 Enantioselective Ketone and β-Keto Ester Hydrogenations (Including Mechanisms) (Takeshi Ohkuma and Ryoji Noyori). 33 Rhodium-Catalyzed Enantioselective Hydrogenation of Functionalized Ketones (Andre Mortreux and Abdallah Karim). 34 Enantioselective Hydrogenation of C=N Functions and Enamines (Felix Spindler and Hans-Ulrich Blaser). 35 Enantioselective Transfer Hydrogenation (A. John Blacker). 36 High-Throughput Experimentation and Ligand Libraries (Johannes G. de Vries and Laurent Lefort). 37 Industrial Applications (Hans-Ulrich Blaser, Felix Spindler, and Marc Thommen). Part V Phase Separation in Homogeneous Hydrogenation. 38 Two-Phase Aqueous Hydrogenations (Ferenc Joo and Agnes Katho). 39 Supercritical and Compressed Carbon Dioxide as Reaction Medium and Mass Separating Agent for Hydrogenation Reactions using Organometallic Catalysts (Walter Leitner). 40 Fluorous Catalysts and Fluorous Phase Catalyst Separation for Hydrogenation Catalysis (Elwin de Wolf and Berth-Jan Deelman). 41 Catalytic Hydrogenation using Ionic Liquids as Catalyst Phase (Peter Wasserscheid and Peter Schulz). 42 Immobilization Techniques (Imre Toth and Paul C. van Geem). Part VI Miscellaneous Topics in Homogeneous Hydrogenation 43 Transition Metal-Catalyzed Regeneration of Nicotinamide Cofactors (Stephan Lutz). 44 Catalyst Inhibition and Deactivation in Homogeneous Hydrogenation (Detlef Heller, Andre H.M. de Vries, and Johannes G. de Vries). 45 Chemical Reaction Engineering Aspects of Homogeneous Hydrogenations (Claude de Bellefon and Nathalie Pestre). Subject Index.
