Modern Oxidation Methods (eBook)

Jan-Erling Bäckvall is Professor of Organic Chemistry at Stockholm University, where he is Head of the Research. He is renowned for his contribution to organopalladium chemistry and catalytic oxidation reactions where he has done mechanistic work and developed new reactions. More recently efficient systems for dynamic kinetic resolution of alcohols based on combined ruthenium and enzyme catalysis were developed in his laboratory. Jan-Erling Bäckvall has published about 380 papers. For his contribution to research he was elected a Member of The Royal Swedish Academy of Sciences, am Member of the Nobel Committee for Chemistry, a Fellow of the Royal Society of Sciences, Sweden, a Member of "Fysiografiska sällskapet" Sweden and a Foreign Member of the Finnish Academy of Science and Letters and received many prizes, awards and honors.

Preface
RECENT DEVELOPMENT IN METAL-CATALYZED DIHYDROXYLATION OF OLEFINS
Introduction
Environmentally Friendly Terminal Oxidants
Supported Osmium Catalysts
Ionic Liquids
Ruthenium Catalysts
Iron Catalysts
Conclusions
TRANSITION METAL-CATALYZED EPOXIDATION OF ALKENES
Introduction
Choice of Oxidant for Selective Epoxidation
Epoxidations of Alkenes Catalyzed by Early Transition Metals
Molybdenum and Tungsten-Catalyzed Epoxidations
Manganese-Catalyzed Epoxidations
Rhenium-Catalzyed Epoxidations
Iron-Catalyzed Epoxidations
Ruthenium-Catalyzed Epoxidations
Epoxidations Using Late Transition Metals
Concluding Remarks
ORGANOCATALYTIC OXIDATION. KETONE-CATALYZED ASYMMETRIC EPOXIDATION OF OLEFINS AND SYNTHETIC APPLICATIONS
Introduction
Catalyst Development
Synthetic Applications
Conclusion
CATALYTIC OXIDATIONS WITH HYDROGEN PEROXIDE IN FLUORINATED ALCOHOL SOLVENTS
Introduction
Properties of Fluorinated Alcohols
Epoxidation of Alkenes in Fluorinated Alcohol Solvents
Sulfoxidation of Thioethers in Fluorinated Alcohol Solvents
Baeyer-Villiger Oxidations of Ketones in Fluorinated Alcohol Solvents
Epilog
MODERN OXIDATION OF ALCOHOLS USING ENVIRONMENTALLY BENIGN OXIDANTS
Introduction
Oxoammonium Based Oxidation of Alcohols - TEMPO as Catalyst
Metal-Mediated Oxidation of Alcohols - Mechanism
Ruthenium-Catalyzed Oxidations with O2
Palladium-Catalyzed Oxidations with O2
Copper-Catalyzed Oxidations with O2
Other Metals as Catalysts for Oxidation with O2
Catalytic Oxidation of Alcohols with Hydrogen Peroxide
Concluding Remarks
AEROBIC OXIDATIONS AND RELATED REACTIONS CATALYZED BY N-HYDROXYPHTHALIMIDE
Introduction
NHPI-Catalyzed Aerobic Oxidation
Functionalization of Alkanes Catalyzed by by NHPI
Carbon-Carbon Bond Forming Reaction via Catalytic Carbon Radicals Generation Assisted by NHPI
Conclusions
RUTHENIUM-CATALYZED OXIDATION FOR ORGANIC SYNTHESIS
Introduction
RuO4-Promoted Oxidation
Oxidation with Low Valent Ruthenium Catalysts and Oxidants
SELECTIVE OXIDATION OF AMINES AND SULFIDES
Introduction
Oxidation of Sulfides to Sulfoxides
Oxidation of Tertiary Amines to N-Oxides
Concluding Remarks
LIQUID PHASE OXIDATION REACTIONS CATALYZED BY POLYOXOMETALATES
Introduction
Polyoxometalates (POMs)
Oxidation with Mono-Oxygen Donors
Oxidation with Peroxygen Compounds
Oxidation with Molecular Oxygen
Heterogenization of Homogeneous Reactions - Solid-Liquid, Liquid-Liquid, and Alternative Reaction Systems
Conclusion
OXIDATION OF CARBONYL COMPOUNDS
Introduction
Oxidation of Aldehydes to Carboxylic Acids
Oxidation of Ketones
MANGANESE CATALYSED OXIDATION WITH HYDROGEN PEROXIDE
Introduction
Bio-Inspired Manganese Oxidation Catalysts
Manganese-Catalyzed Bleaching
Epoxidationand cis-Dihydroxylation of Alkenes
Manganese Catalysts for the Oxidation of Alkanes, Alcohols, and Aldehydes
Conclusions
BIOOXIDATION WITH CYTOCHROME P450 MONOOXYGENASES
Introduction
Properties of Cytochrome P450 Monooxygenases
Application and Engineering of P450s for the Pharmaceutical Industry
Application of P450s for Synthesis of Fine Chemicals
Engineering of P450s for Biocatalysis
Future Trends