Sheldon R.A., Arends I., Hanefeld U. Green chemistry and catalysis

Wiley VCH, 2007. — 198 p. ISBN: 978-3-527-30715-9Introduction: Green Chemistry and CatalysisE Factors and Atom Efficiency
The Role of Catalysis
The Development of Organic Synthesis
Catalysis by Solid Acids and Bases
Catalytic Reduction
Catalytic Oxidation
Catalytic C–C Bond Formation
The Question of Solvents: Alternative Reaction Media
Biocatalysis
Renewable Raw Materials and White Biotechnology
Enantioselective Catalysis
Risky Reagents
Process Integration and Catalytic CascadesSolid Acids and Bases as CatalystsSolid Acid Catalysis
Acidic Clays
Zeolites and Zeotypes: Synthesis and Structure
Zeolite-catalyzed Reactions in Organic Synthesis
Electrophilic Aromatic Substitutions
Additions and Eliminations
Rearrangements and Isomerizations
Cyclizations
Solid Acids Containing Surface SO3H Functionality
Heteropoly AcidsSolid Base Catalysis
Anionic Clays: Hydrotalcites
Basic Zeolites
Organic Bases Attached to Mesoporous Silicas
Other ApproachesCatalytic ReductionsHeterogeneous Reduction Catalysts
General Properties
Transfer Hydrogenation Using Heterogeneous Catalysts
Chiral Heterogeneous Reduction Catalysts
Homogeneous Reduction Catalysts
Wilkinson Catalyst
Chiral Homogeneous Hydrogenation Catalysts and Reduction
of the C= C Double Bond
Chiral Homogeneous Catalysts and Ketone Hydrogenation
Imine Hydrogenation
Transfer Hydrogenation using Homogeneous Catalysts
Biocatalytic ReductionsEnzyme Technology in Biocatalytic Reduction
Whole Cell Technology for Biocatalytic Reduction
ConclusionsCatalytic OxidationsMechanisms of Metal-catalyzed Oxidations:
General Considerations
Homolytic Mechanisms
Direct Homolytic Oxidation of Organic Substrates
Heterolytic Mechanisms
Catalytic Oxygen Transfer
Ligand Design in Oxidation Catalysis
Enzyme Catalyzed Oxidations
Alkenes
Epoxidation
Tungsten Catalysts
Rhenium Catalysts
Ruthenium Catalysts
Manganese Catalysts
Iron Catalysts
Selenium and OrganocatalystsHydrotalcite and Alumina Systems
Biocatalytic Systems
Vicinal Dihydroxylation
Oxidative Cleavage of Olefins
Oxidative Ketonization
Allylic Oxidations
Alkanes and Alkylaromatics
Oxidation of Alkanes
Oxidation of Aromatic Side Chains
Aromatic Ring Oxidation
Oxygen-containing Compounds
Oxidation of Alcohols
Palladium-catalyzed Oxidations with O2
Gold Catalysts
Copper Catalysts
Other Metals as Catalysts for Oxidation with O2
Catalytic Oxidation of Alcohols with Hydrogen Peroxide
Oxoammonium Ions in Alcohol Oxidation
Biocatalytic Oxidation of Alcohols
Oxidative Cleavage of 1,2-Diols
Carbohydrate Oxidation
Oxidation of Aldehydes and Ketones
Baeyer-Villiger Oxidation
Oxidation of Phenols
Oxidation of Ethers
Heteroatom Oxidation
Oxidation of Amines
Primary Amines
Secondary Amines
Tertiary Amines
Amides
Sulfoxidation
Asymmetric Oxidation
Asymmetric Epoxidation of Olefins
Asymmetric Dihydroxylation of Olefins
Asymmetric Sulfoxidation
Asymmetric Baeyer-Villiger OxidationCatalytic Carbon–Carbon Bond FormationEnzymes for Carbon–Carbon Bond Formation
Enzymatic Synthesis of CyanohydrinsHydroxynitrile Lyases
Lipase-based Dynamic Kinetic Resolution
Enzymatic Synthesis of -Hydroxyketones (Acyloins)
Enzymatic Synthesis of -Hydroxy Acids
Enzymatic Synthesis of Aldols
( -Hydroxy Carbonyl Compounds)
DHAP-dependent Aldolases
PEP- and Pyruvate-dependent Aldolases
Glycine-dependent Aldolases
Acetaldehyde-dependent Aldolases
Enzymatic Synthesis of -Hydroxynitriles
Transition Metal Catalysis
Carbon Monoxide as a Building Block
Carbonylation of R–X (CO Insertion/R-migration)
Aminocarbonylation
Hydroformylation or Oxo Reaction
Hydroaminomethylation
Methyl Methacrylate via Carbonylation Reactions
Heck-type Reactions
Heck Reaction
Suzuki and Sonogashira Reaction
Metathesis
Metathesis involving Propylene
Ring-opening Metathesis Polymerization (ROMP)
Ring-closing Metathesis (RCM)
Conclusion and OutlookHydrolysisStereoselectivity of Hydrolases
Hydrolase-based Preparation of Enantiopure Compounds
Kinetic Resolutions
Dynamic Kinetic Resolutions
Kinetic Resolutions Combined with Inversions
Hydrolysis of Symmetric Molecules and the meso-trickHydrolysis of Esters
Kinetic Resolutions of Esters
Dynamic Kinetic Resolutions of Esters
Kinetic Resolutions of Esters Combined with Inversions
Hydrolysis of Symmetric Esters and the meso-trick
Hydrolysis of Amides
Production of Amino Acids by (Dynamic) Kinetic Resolution
The Acylase Process
The Amidase Process
VIII Contents
The Hydantoinase Process
Cysteine
Enzyme-catalysed Hydrolysis of Amides
Enzyme-catalysed Deprotection of Amines
Hydrolysis of Nitriles
Nitrilases
Nitrile Hydratases
Conclusion and OutlookCatalysis in Novel Reaction MediaWhy use a solvent?
Choice of Solvent
Alternative Reaction Media and Multiphasic Systems
Two Immiscible Organic Solvents
Aqueous Biphasic Catalysis
Olefin Hydroformylation
Hydrogenation
Carbonylations
Other C–C Bond Forming Reactions
Oxidations
Fluorous Biphasic Catalysis
Olefin Hydroformylation
Other Reactions
Supercritical Carbon Dioxide
Supercritical Fluids
Supercritical Carbon Dioxide
Hydrogenation
Oxidation
Biocatalysis
Ionic Liquids
Biphasic Systems with Supercritical Carbon Dioxide
Thermoregulated Biphasic Catalysis
Conclusions and ProspectsChemicals from Renewable Raw MaterialsCarbohydrates
Chemicals from Glucose via Fermentation
Ethanol
Microbial Production of Ethanol
Green Aspects
Lactic Acid
Contents IX
1,3-Propanediol
3-Hydroxypropanoic Acid
Synthesizing Aromatics in Nature’s Way
Aromatic -Amino Acids
Indigo: the Natural Color
Pantothenic Acid
The -Lactam Building Block 7-Aminodesacetoxycephalosporanic
Acid
Riboflavin
Chemical and Chemoenzymatic Transformations of Carbohydrates
into Fine Chemicals and Chiral Building Blocks
Ascorbic Acid
Carbohydrate-derived C3 and C4 Building Blocks
5-Hydroxymethylfurfural and Levulinic Acid
Fats and Oils
Biodiesel
Fatty Acid Esters
Terpenes
Renewable Raw Materials as Catalysts
Green Polymers from Renewable Raw Materials
Concluding RemarksProcess Integration and Cascade CatalysisDynamic Kinetic Resolutions by Enzymes Coupled
with Metal Catalysts
Combination of Asymmetric Hydrogenation
with Enzymatic Hydrolysis
Catalyst Recovery and Recycling
Immobilization of Enzymes: Cross-linked Enzyme Aggregates
(CLEAs)
Conclusions and ProspectsEpilogue: Future Outlook
Green Chemistry: The Road to Sustainability
Catalysis and Green Chemistry
The Medium is the Message
Metabolic Engineering and Cascade Catalysis
Concluding Remarks