Heterogeneous Catalysis in Organic Transformations

Cover
Half Title
Series Page
Title Page
Copyright Page
Table of Contents
Preface
Editors
Contributors
Chapter 1: Introduction to Heterogeneous Catalysis in Organic Transformation
1.1 Introduction
1.2 Types of Catalysts
1.2.1 Homogeneous Catalyst
1.2.2 Heterogeneous Catalyst
1.2.3 Heterogenized Homogeneous Catalysts
1.2.4 Biocatalysts
1.3 Origin of Heterogeneous Catalysis
1.4 Comparison between Homogeneous and Heterogeneous Catalysis
1.5 Contribution of Heterogeneous Catalysis
1.6 Mechanism of Heterogeneous Catalysis
1.6.1 Langmuir–Hinshelwood Mechanism
1.6.2 Eley–Rideal Mechanism
1.6.3 Harris–Kasemo Mechanism
1.7 Categorization of Heterogeneous Catalysts
1.7.1 Catalysts Having Basic Sites
1.7.2 Catalysts Having Acidic Sites
1.8 Characterization Techniques Needed for Heterogeneous Catalysts
1.8.1 X-Ray Diffraction
1.8.2 X-Ray Absorption Spectroscopy
1.8.3 Electron Microscopy
1.8.4 Nuclear Magnetic Resonance
1.8.5 Electron Spin Resonance Microscopy
1.9 Significance of Heterogeneous Catalysis
References
Chapter 2: Oxide Nanoparticles in Heterogeneous Catalysis
2.1 Introduction
2.2 Application of NPs
2.2.1 Applications in Drugs and Medications
2.2.2 Applications in Manufacturing and Materials
2.2.3 Applications in the Environment
2.2.4 Applications in Electronics
2.2.5 Application in Catalysis
2.3 Copper Oxide Nanoparticle-catalyzed Organic Reactions
2.3.1 Carbon–Carbon Bond Formation
2.3.1.1 Stille Coupling Reaction
2.3.1.2 Arylation of Active Methylene Compounds
2.3.2 Carbon–Nitrogen Bond Formation
2.3.2.1 N-Arylation Reaction
2.3.2.2 Arylation of Aromatic Heterocycles
2.3.2.3 Amidation of Aryl Iodides
2.3.2.4 Intramolecular Carbon–Nitrogen Bond Formation
2.3.3 Carbon–Oxygen Bond Formation
2.3.3.1 Oxygen Arylation
2.3.4 Carbon–Sulfur Bond Formation
2.3.4.1 Carbon–Sulfur Cross-Coupling Reaction between Thiols and Iodobenzene
2.3.4.2 Stereoselective Synthesis of Vinyl Sulfides Catalyzed by using CuO Nanoparticles
2.3.5 Carbon–Selenium Bond Formation
2.4 Zinc Oxide Nanoparticle-Catalyzed Organic Reactions
2.4.1 Synthesis of Nitrogen-containing Heterocycles
2.4.1.1 Synthesis of Polysubstituted Pyrroles
2.4.1.2 Synthesis of Benzimidazoles
2.4.1.3 Synthesis of Imidazo-fused Polyheterocycles
2.4.1.4 Synthesis of Quinoxalines
2.4.2 Synthesis of Oxygen-containing Heterocycles
2.4.2.1 Synthesis of Furan Derivatives
2.4.2.2 Synthesis of coumarin
2.4.2.3 Synthesis of Xanthenes
2.4.3 Synthesis of Other Heterocycles
2.4.3.1 Synthesis of 6-amino-5-cyano-pyrano[2,3-c] Pyrazoles
2.4.3.2 Synthesis of Structurally Diverse Pyridine Derivatives
2.4.3.3 Synthesis of 2-thioxo-1,3-oxazoles Derivatives
2.4.3.4 Synthesis of Bis-isoquinolinones
2.5 Titanium oxide nanoparticle-catalyzed organic reactions
2.5.1 Strecker Reaction Catalyzed by Nano-TiO 2 P25
2.5.2 Synthesis of 2,3-disubstituted Dihyrdoquinazolin-4(1H)-ones
2.5.3 Friedel–Crafts Alkylation of Indoles with Epoxides Catalyzed by Nanocrystalline Titanium(IV) Oxide
2.5.4 Synthesis of Polysubstituted Pyrrolidinones
2.5.5 Synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazole
2.6 Nickel Oxide Nanoparticles in Organic Transformations
2.6.1 Synthesis of Spiro and Condensed Indole Derivatives
2.6.2 Amidoalkyl Naphthol Derivatives Synthesis
2.6.3 Synthesis of Diindolyl Oxindole Derivatives in Aqueous Medium
2.7 Transition Metal Ferrites in Organic Reactions
2.7.1 Cobalt Ferrite
2.7.1.1 Oxidation Reactions
2.7.1.1.1 Oxidation of Alcohol
2.7.1.1.2 Oxidation of Hydrocarbon
2.7.1.2 Coupling Reactions
2.7.1.2.1 Carbon–Oxygen Bond
2.7.1.2.2 Carbon–Carbon Bond (Suzuki Coupling)
2.7.1.2.3 Carbon–Sulfur Bond
2.7.1.3 Ring-opening Reaction of Epoxides
2.7.1.4 Knoevenagel Condensation
2.7.1.5 Ritter Reaction
2.7.1.6 Synthesis of 5-hydroxymethylfurfural
2.7.2 Copper Ferrite Nanoparticles
2.7.2.1 Synthesis of 1,4-dihydropyridines
2.7.2.2 Synthesis of α-aminonitriles
2.7.2.3 Ullmann C–O Coupling Reaction
2.7.2.4 Synthesis of β,γ-unsaturated Ketones
2.7.2.5 Direct C–H Amination of Benzothiazoles
2.7.2.6 Synthesis of 9-substituted Aryl-1,8-dioxo-octahydroxanthenes
2.7.3 Nickel Ferrite Nanoparticles
2.7.3.1 C–O Bond Formation
2.7.4 Zinc Ferrite Nanoparticles
2.8 Mixed metal oxides nanoparticles
2.8.1 MgO-ZrO 2 -mixed Metal Oxide Nanoparticle
2.8.1.1 Cross Aldol Reaction
2.8.1.2 N-benzyloxycarbonylation of Amines
2.8.1.3 Reduction of Aromatic Nitro Compounds
2.8.1.4 Synthesis of 1,5-benzodiazepines
2.8.1.5 Synthesis of Tinidazole
2.8.1.6 Oxidation of 2,6-dimethyl Phenol
2.8.1.7 Synthesis of 1,4-dihydropyridines
References
Chapter 3: Noble Metal Nanoparticles in Organic Catalysis
3.1 Introduction
3.2 Organic Catalysis by using Au NP
3.2.1 Oxidation Reactions
3.2.1.1 Oxidation of Aliphatic Alcohols
3.2.1.2 Oxidation of Diols
3.2.1.3 Oxidation of Polyols
3.2.1.4 Oxidation of Amino Alcohols
3.2.1.5 Oxidation of Cycloalcohols
3.2.1.6 Oxidation of Aromatic Alcohols
3.2.1.7 Oxidation of Alkanes
3.2.1.7.1 Oxidation of Cyclohexane to Adipic Acid
3.2.2 Epoxidation Reaction
3.2.3 Hydrogenation Reactions
3.2.3.1 Hydrogenation Reactions of Alkenes, Dienes and Alkynes
3.2.3.2 Hydrogenation of α,β-unsaturated Carbonyl Groups
3.3 Organic Catalysis by using Au NP
3.3.1 Pd/rGO NP for Reduction of Nitroarenes
3.3.2 Monodisperse Pd/GO for Suzuki Cross-coupling Reaction
3.3.3 Hydrogenation of Unsaturated Compounds by Pd@GO Catalyst
3.3.4 Pd NP/Polythiophene Nanospheres as Heterogeneous Catalysts
3.4 Catalytic Reactions by Ir-based NP
3.4.1 Ir NPs as Catalysts for Hydrogenation and Hydrogen Production
3.5 Catalytic Reactions by Pt-based NP
3.5.1 Catalytic Applications of Pt NP
3.6 Catalytic Reactions by Ag-based NP
3.6.1 Application of Ag NP
3.6.1.1 Reduction of Nitroaromatics
3.6.1.2 Reduction of Carbonyl Compounds
3.6.1.3 Other Reductive Transformations
3.6.1.4 Oxidation of Alcohols
3.6.1.5 Oxidation of Silanes
3.6.1.6 Oxidation of Olefins
3.6.1.7 Alkylation of Amines and Arenes
3.6.1.8 Miscellaneous Applications
3.6.1.8.1 Ag NP-catalysed Green Synthesis and Reduction of Methylene Blue Dye
3.6.2 Magnetic NP
3.6.2.1 Future Perspectives
References
Chapter 4: Organometallic Compounds as Heterogeneous Catalysts
4.1 Introduction
4.2 Organocopper Compounds
4.3 Reactions with Organocopper Compounds
4.3.1 Synthesis of β-methylthiobutenolides
4.3.2 Epoxide Ring Opening
4.3.3 Conjugate Addition
4.3.4 Preparation of Allenes
4.3.5 Coupling with Acyl Chloride
4.3.6 Ring-opening Reaction of α,β-epoxy silane
4.3.7 Reaction of Organocuprate with α,β-unsaturated Ketone
4.3.8 Synthesis of β-amino acid
4.3.9 Substitution Reaction
4.3.10 Remote Asymmetric Induction
4.3.11 Organolithium compounds
4.3.12 Synthetic methods for organolithium compounds
4.4 Reactions with Organolithium Compounds
4.4.1 Addition Reactions
4.4.2 Synthesis of 1,4-diketones
4.4.3 Reductive Coupling of Aldehyde Tosylhydrazones
4.4.4 Parham Cyclization
4.4.5 Wittig Rearrangement
4.4.6 Ramberg–Bäckland Reaction
4.4.7 Synthesis of 1,5-diketones
4.4.8 Rearrangement Reaction
4.4.9 Synthesis of α,β-butenolides
4.4.10 Reaction with Epoxy Silane
4.4.11 Organozinc Compounds
4.4.12 Synthetic Methods for Organozinc Compounds
4.5 Reactions with Organozinc Compounds
4.5.1 Addition of Organozinc Reagent to β-keto phosphonates
4.5.2 Synthesis of 1,3-dienes
4.5.3 Negishi Cross-coupling Reaction
4.5.4 Alkylative Ring Opening
4.5.5 Addition of Dialkyl Zinc to Aldehydes
4.5.6 Synthesis of Allenes
4.5.7 Preparation of Polyfunctional Nitriles
4.5.8 Synthesis of Cyclopentenone
4.5.9 Geminal-functionalization of Cyclopropanes
4.5.10 Nucleophilic Substitution Reaction
4.5.11 Organoselenium Compounds
4.5.12 Synthetic Methods for Organoselenium Compounds
4.6 Reactions with Organoselenium Compounds
4.6.1 Suzuki–Miyaura Carbon–Carbon Cross-coupling Reaction
4.6.2 Sonogashira Coupling
4.6.3 Aldehyde–Alkyne–Amine (A 3) Coupling Reaction
4.6.4 Oxidation of Cyclohexene
4.6.5 Heck Reaction
References
Chapter 5: Solid-supported Catalyst in Heterogeneous Catalysis
5.1 Introduction
5.2 Supported Catalysts
5.3 Solid Supports
5.3.1 Silicon Carbide Support
5.3.2 Metal Oxide Supports
5.3.3 Surface-modified Oxides as Supports
5.3.4 Sulfide Supports
5.3.5 Metal Supports
5.4 Hybrid Catalysts
5.5 Types of Hybrid Catalysts
5.5.1 Heterogeneous–Homogeneous Hybrid
5.5.2 Heterogeneous–Enzyme Hybrid
5.5.3 Ship-in-a-bottle Catalyst
5.5.4 Polymerization Catalyst
5.5.5 Coated Catalysts
5.6 Some examples of supported catalysts
5.6.1 Titanium Oxide as a Catalyst Support in Heterogeneous Catalysis
5.6.2 Au/TiO 2 Heterogeneous Catalyst
5.6.3 Ni/TiO 2 Heterogeneous Catalyst
5.6.4 TiO 2 Support in Bimetallic Heterogeneous Catalysis
5.6.5 Heterogeneous Metal Catalysts for Oxidation Reactions
5.6.6 Conversion of Glucose to Gluconic Acid
5.6.7 Oxidation of Carbon Monoxide
5.6.8 Oxidation of Alkyl-substituted Benzene
5.6.9 Total Oxidation of Formaldehyde
5.6.10 Epoxidation of Olefins by Molecular Oxygen over Supported Metal Heterogeneous Catalysts
5.7 Transition metal complexes with polymeric ligands
References
Chapter 6: Mesoporous Materials in Heterogeneous Catalysis
6.1 Introduction
6.2 Types and Classification of Mesoporous Materials
6.3 Characteristic Features of Mesoporous Materials for Catalysis
6.4 Building Blocks of MOFs
6.5 Basic Underlying Principles of Heterogeneous Catalysis with MOFs
6.5.1 Unsaturated Metal Centre
6.5.2 Surface Modification or Functionalisation of Linker Unit
6.5.3 Central Pore/Cavity of MOFs
References
Chapter 7: Role of Metal-heterogeneous Catalysts in Organic Synthesis
7.1 Heterogeneous Catalysts in Organic Synthesis
7.2 Palladium-based Heterogeneous Catalysts
7.3 Platinum-based Heterogeneous Catalysts
7.4 Ruthenium-based Heterogeneous Catalysts
7.5 Titanium-based Heterogeneous Catalysts
7.6 Rhodium-based Heterogeneous Catalysts
7.7 Mixed Metal-based Heterogeneous Catalysts
References
Index