Metal-Catalyzed Reactions in Water

PREFACE

METAL-CATALYZED CROSS-COUPLINGS OF ARYL HALIDES TO FORM C - C BONDS IN AQUEOUS MEDIA
Introduction
Aqueous-Phase Cross-Coupling Using Hydrophilic Catalysts
Cross-Coupling in Aqueous Media Using Hydrophobic Ligands
Heterogeneous Catalysts in Aqueous Media
Special Reaction Conditions
Homogeneous Aqueous-Phase Modification of Biomolecules
Conclusion

METAL-CATALYZED C - H BOND ACTIVATION AND C - C BOND FORMATION IN WATER
Introduction
Catalytic Formation of C - C Bonds from spC - H Bonds in Water
Activation of sp2C - H Bonds for Catalytic C - C Bond Formation in Water
Activation of sp3C - H Bonds for Catalytic C - C Bond Formation in Water
Conclusion

CATALYTIC NUCLEOPHILIC ADDITIONS OF ALKYNES IN WATER
Introduction
Catalytic Nucleophilic Additions of Terminal Alkynes with Carbonyl Derivatives
Addition of Terminal Alkyne to Imine, Tosylimine, Iminium Ion, and Acyl Iminium Ion
Direct Conjugate Addition of Terminal Alkynes
Conclusions

WATER-SOLUBLE HYDROFORMYLATION CATALYSIS
Introduction
Hydroformylation of Light C2 - C5 Alkenes in the RCH/RP Process
Hydroformylation of Alkenes Heavier than C5
Innovative Expansions
Conclusion

GREEN CATALYTIC OXIDATIONS IN WATER
Introduction
Examples of Water-Soluble Ligands
Enzymatic Oxidations
Biomimetic Oxidations
Epoxidation, Dihydroxylation, and Oxidative Cleavage of Olefins
Alcohol Oxidations
Sulfoxidations in Water
Conclusions and Future Outlook

HYDROGENATION AND TRANSFER HYDROGENATION IN WATER
Introduction
Water-Soluble Ligands
Hydrogenation in Water
Transfer Hydrogenation in Water
Role of Water
Concluding Remarks

CATALYTIC REARRANGEMENTS AND ALLYLATION REACTIONS IN WATER
Introduction
Rearrangements
Allylation Reactions
Conclusion

ALKENE METATHESIS IN WATER
Introduction
Examples of Applications of Olefin Metathesis in Aqueous Media
Conclusions and Outlook

NANOCATALYSIS IN WATER
Introduction
Nanocatalysis
Effects of Size of Nanocatalysts
Transition-Metal Nanoparticles
Catalytic Applications of Transition-Metal-Based Nanomaterials
Pd Nanoparticles in Organic Synthesis
Nanogold Catalysis
Copper Nanoparticles
Ruthenium Nanocatalysts
Magnetic Iron Oxide Nanoparticle
Cobalt Nanoparticles
Conclusion

INDEX

Pierre H. Dixneuf is Emeritus Professor of Chemistry at the University of Rennes, Bretagne, France, where he built a team working on organometallic chemistry and catalysis, and founded the Research Institute of Chemistry of Rennes. He developed several catalytic processes based on innovative ruthenium catalysts: selective transformations of alkynes and incorporation of CO2, ruthenium-vinylidenes and -allenylidenes in catalysis, catalytic synthesis of heterocycles, alkene metathesis catalysts and transformation of plant oils, C - H bond activation/functionalization including in water. He has designed new ruthenium catalysts especially involving metal-carbene bonds. He was research advisor at both CNRS and University of Rennes. He has authored/co-authored more than 400 publications, and is a member of the Institute Universitaire de France (IUF). His work has been acknowledged with several prizes including: A. v Humboldt, Le Bel, Grignard-Wittig, Sacconi medal, prix IFP of Académie des Sciences.

Victorio Cadierno received his PhD degree from the University of Oviedo (Spain) in 1996 under the supervision of Prof. J. Gimeno. He then joined the group of Dr. J. P. Majoral at the Laboratoire de Chimie de Coordination (LCC-CNRS) in Toulouse (France) for a two-year postdoctoral stay. Thereafter, he returned to the University of Oviedo where he is currently Associate Professor of Inorganic Chemistry. In 2002 he received the Young Investigator Award from the Spanish Royal Society of Chemistry (RSEQ). His research interests cover the chemistry
of ruthenium complexes and their catalytic applications, with special focus on atom economical processes both in organic solvents and aqueous media. He has published more than 130 articles, reviews and book chapters in these fields.

P. Dixneuf, Université de Rennes 1, Rennes, France; V. Cadierno, University of Oviedo, Oviedo, Spain