Alkane Functionalization

 
 
Standards Information Network (Verlag)
  • 1. Auflage
  • |
  • erschienen am 19. Dezember 2018
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  • 648 Seiten
 
E-Book | PDF mit Adobe-DRM | Systemvoraussetzungen
978-1-119-37923-2 (ISBN)
 
Presents state-of-the-art information concerning the syntheses of valuable functionalized organic compounds from alkanes, with a focus on simple, mild, and green catalytic processes Alkane Functionalization offers a comprehensive review of the state-of-the-art of catalytic functionalization of alkanes under mild and green conditions. Written by a team of leading experts on the topic, the book examines the latest research developments in the synthesis of valuable functionalized organic compounds from alkanes. The authors describe the various modes of interaction of alkanes with metal centres and examine theoxidative alkane functionalization upon C-O bond formation. They address the many types of mechanisms, discuss typical catalytic systems and highlight the strategies inspired by biological catalytic systems. The book also describes alkane functionalization upon C-heteroatom bond formation as well as oxidative and non-oxidative approaches. In addition, the book explores non-transition metal catalysts and metal-free catalytic systems and presents selected types of functionalization of sp3 C-H bonds pertaining to substrates other than alkanes. This important resource: * Presents a guide to the most recent advances concerning the syntheses of valuable functionalized organic compounds from alkanes * Contains information from leading experts on the topic * Offers information on the catalytic functionalization of alkanes that allows for improved simplicity and sustainability compared to current multi-stage industrial processes * Explores the challenges inherent with the application of alkanes as starting materials for syntheses of added value functionalized organic compounds Written for academic researchers and industrial scientists working in the fields of coordination chemistry, organometallic chemistry, catalysis, organic synthesis and green chemistry, Alkane Functionalization is an important resource for accessing the most up-to-date information available in the field of catalytic functionalization of alkanes.
1. Auflage
  • Englisch
  • Newark
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  • Großbritannien
John Wiley & Sons Inc
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  • 37,35 MB
978-1-119-37923-2 (9781119379232)
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ARMANDO J. L. POMBEIRO is full professor at the Instituto Superior Tecnico (IST) of the Universidade de Lisboa (ULisboa), Portugal. He is President of the College of Chemistry of ULisboa and of the Centro de Quimica Estrutural (IST), Director of the Catalysis and Sustainability (CATSUS) PhD program, and full member of the Academy of Sciences of Lisbon. His research addresses activation of small molecules with industrial, environmental or biological significance, including metal-mediated synthesis and catalysis (e.g., functionalization of alkanes), self-assembly of polynuclear and supramolecular structures, non-covalent interactions in synthesis, crystal engineering of coordination compounds, molecular electrochemistry and theoretical studies. He authored or edited 7 books, (co-)authored over 800 research publications and 40 patents. His work has received over 20,000 citations and he has an h index of over 60 (Web of Science). He is the recipient of several scientific prizes, including from the Chemical Societies of France, Royal Spanish and Portugal, as well as from the Technical University of Lisbon, and the Vanadis Award.

M. FATIMA C. GUEDES DA SILVA is an Associate Professor at Instituto Superior Tecnico, Lisbon, Portugal. She is the Coordinator of the research group of Coordination Chemistry and Catalysis of the Centro de Quimica Estrutural, member of the Coordination Commission of this Centre and of the Directive Board of the Catalysis and Sustainability (CATSUS) PhD program. Her main research interests include: structural determination, by X-ray diffraction analysis, of metal complexes and organic compounds, metal polynuclear assemblies and supramolecular structures; activation, by transition metal centres, of small molecules with biological, pharmacological, environmental or industrial significance; metal mediated synthesis and catalysis; molecular electrochemistry and electrocatalysis; mechanistic investigation of fast reactions mainly by digital simulation of cyclic voltammetry. She co-authored ca. 300 research publications, 13 patents. She was awarded the Scientific Prize Universidade de Lisboa / CGD and the Scientific Prize of the Portuguese Electrochemical Society.
  • Cover
  • Title Page
  • Copyright
  • Contents
  • List of Contributors
  • About the Editors
  • Preface
  • List of Abbreviations
  • Chapter 1 Alkane Functionalization: Introduction and Overview
  • 1.1 Why Alkane Functionalization?
  • 1.2 Alkane Functionalization as a Challenge and Overcoming Approaches
  • 1.3 Types of Alkane Functionalization
  • 1.4 Structure of the Book
  • 1.5 Final Remarks
  • Acknowledgments
  • Part I C-O Bond Formation. Hydroxylation and Other Oxygenatio
  • Chapter 2 Activation and Oxidative Functionalization of Alkanes with Noble-Metal Catalysts: Molecular Mechanisms
  • 2.1 Introduction
  • 2.2 Activation of C-H Bond in Alkanes
  • 2.3 Activation of Dioxygen
  • 2.3.1 Peroxo Complexes
  • 2.3.2 Hydroperoxo Complexes
  • 2.3.3 Oxo Complexes
  • 2.4 Design of Catalytic Systems for Oxidation of Alkanes
  • 2.5 Oxidation of Alkanes with Metal Complexes in Solution
  • 2.5.1 Shilov's System and Other Pt Catalysts
  • 2.5.2 Oxidation of Alkanes with Pd Compounds
  • 2.5.3 Rh-Containing Catalysts and Catalytic Systems
  • 2.6 Final Comments
  • References
  • Chapter 3 Alkane-Oxidizing Systems Based on Metal Complexes. Radical Versus Nonradical Mechanisms1
  • 3.1 Introduction
  • 3.2 Main Features of Oxidation Processes
  • 3.2.1 Radical Reactions, But Not Radical-Chain Reactions
  • 3.2.2 Hydrogen Peroxide Decomposition to Generate Hydroxyl Radicals
  • 3.2.3 Possible Mechanisms of H2O2 Decomposition
  • 3.2.4 Activated Adducts (Transition States) Containing Simultaneously Two H2O2 Molecules
  • 3.3 Methods of Mechanism Investigation
  • 3.3.1 Formation of Alkyl Hydroperoxides
  • 3.3.2 Regioselectivity
  • 3.3.3 Competitive Oxidation of an Alkane and Solvent
  • 3.3.4 Shul'pin Test for Alkyl Hydroperoxides
  • 3.4 Conclusions
  • References
  • Chapter 4 Reactions of Alkyl Radicals in Aqueous Solutions*
  • 4.1 Introduction
  • 4.2 Production of Alkyl Radicals in Aqueous Solutions
  • 4.2.1 The Fenton and Fenton-like Reactions
  • 4.2.2 Other Oxidation Reactions
  • 4.2.3 Reduction Reactions
  • 4.2.4 Reactions with Other Radicals
  • 4.2.4.1 Inorganic Radicals
  • 4.2.4.2 Organic Radicals
  • 4.3 Electrochemistry
  • 4.3.1 Radicals as the Products of the Direct Oxidations of Substrates on the Electrode
  • 4.3.2 Radicals as the Products of the Direct Reductions of Substrates on the Electrode
  • 4.3.3 Radicals as the Products of Electro-Catalytic Oxidations
  • 4.3.4 Radicals as the Products of Electro-Catalytic Reductions
  • 4.4 Photochemistry
  • 4.4.1 Light Absorption that Leads Directly to the Dissociation of an R X Bond
  • 4.4.2 Photolytic Formation of Active Species that React to Form Alkyl Radicals
  • 4.4.3 Photosensitized Processes
  • 4.4.4 Photocatalytic Processes Initiated by Light Absorption in Semiconductors
  • 4.5 Ionizing Radiation
  • 4.6 Sono-Chemistry
  • 4.7 Mechano-Chemistry
  • 4.8 Microwave Chemistry
  • 4.9 Production of Alkyl Radicals in Biological Systems
  • 4.9.1 Enzymatic Processes
  • 4.9.2 Processes Initiated by ROS/RNS
  • 4.10 General Comments on Radical Reactions
  • 4.10.1 Nearly All Radicals Are Both Oxidizing and Reducing Agents
  • 4.10.2 Nearly All Redox Processes Involving Alkyl Radicals Proceed Via the Bridged Mechanism and Not Via the Outer-Sphere Mechanism
  • 4.10.3 Three Electron-2 Center, Hemi-, Bonds
  • 4.10.4 Radical-Radical Reactions
  • 4.10.5 Measuring the Lifetime of Very Short-Lived Radicals
  • 4.11 Unimolecular Reactions
  • 4.11.1 Isomerization Reactions
  • 4.11.2 &rmbeta
  • -Eliminations
  • 4.11.3 Methyl Radical Eliminations
  • 4.12 Reactions of Alkyl Radicals with Different Substrates
  • 4.12.1 Reactions with Radicals
  • 4.12.2 Reactions with Organic Substrates
  • 4.12.3 Reduction or Oxidation Processes
  • 4.12.4 Reactions with Dioxygen
  • 4.12.5 Reactions with Low-Valent Transition-Metal Complexes Forming Complexes with Metal-Carbon Bonds
  • 4.12.6 Reactions with Surfaces and Nanoparticles
  • 4.13 Concluding Remarks
  • Acknowledgments
  • References
  • Chapter 5 C-H Bond Oxidation with Transition-Metal-Based Carbene Complexes
  • 5.1 Introduction
  • 5.2 Iron-Catalyzed C-O Bond Formation
  • 5.3 Iridium-Catalyzed C-O Bond Formation
  • 5.4 Palladium- and Platinum-Catalyzed C-O Bond Formation
  • 5.5 Final Comments
  • Acknowledgments
  • References
  • Chapter 6 Alkane Oxidation with C-Scorpionate Metal Complexes
  • 6.1 Introduction
  • 6.2 C-Scorpionate Complexes
  • 6.3 Oxidation of Cyclohexane to KA Oil
  • 6.3.1 Oxidation of Cyclohexane at Nonconventional Conditions
  • 6.3.2 Oxidation of Cyclohexane Catalyzed by Supported C-Scorpionate Complexes
  • 6.4 Oxidation of Cyclohexane to Adipic Acid
  • 6.5 Oxidation of Other Hydrocarbons
  • Acknowledgments
  • References
  • Chapter 7 Alkane Oxidation with Multinuclear Heterometallic Catalysts
  • 7.1 Introduction
  • 7.2 Peroxidative Oxidation of Liquid Alkanes
  • 7.3 Intramolecular C-H Oxygen Insertion
  • 7.4 Peroxidative Hydrocarboxylation of Light and Liquid Alkanes
  • 7.5 Concluding Remarks
  • Acknowledgments
  • References
  • Chapter 8 Oxidative Functionalization of Methane on Heterogeneous Catalysts
  • 8.1 Introduction
  • 8.2 Oxidative Routes for Methane Functionalization
  • 8.2.1 High-Temperature Routes
  • 8.2.1.1 Partial Oxidation of Methane to Methanol and Formaldehyde
  • 8.2.1.2 Oxidative Coupling of Methane (OCM)
  • 8.2.2 Low-Temperature Routes
  • 8.2.2.1 Halogenation of Methane
  • 8.2.2.2 Oxyhalogenation of Methane
  • 8.2.2.3 Selective Oxidation of Methane
  • 8.3 Challenges in the Direct Oxidation of Methane to Methanol
  • 8.4 Strategies and Catalysts for the Selective Oxidation of Methane to Methanol
  • 8.5 Zeolite-Based Catalysts for the Oxidation of Methane to Methanol
  • 8.5.1 Fe-Zeolites
  • 8.5.2 Cu-Zeolites
  • 8.5.2.1 Structure of Active Sites
  • 8.5.2.2 Activity of Explored Cu-Zeolites
  • 8.6 Approaches to Increase Methanol Yields on Cu-Zeolites
  • 8.6.1 Synthetic Strategies for Highly Active Cu-Zeolites
  • 8.6.2 Methanol Production over Cu-Zeolites in Catalytic Mode
  • 8.6.3 Alternative Catalyst Components
  • 8.7 Outlook
  • Acknowledgments
  • References
  • Chapter 9 Gas-Phase Oxidation of Alkanes
  • 9.1 The Gas-Phase Oxidation of Alkanes
  • 9.2 Oxidation of Isobutane to Methacrylic Acid
  • 9.2.1 Polyoxometalates Catalysts
  • 9.2.2 Other Synthetic Pathways to Methacrylic Acid
  • 9.2.3 Current Industrial Synthesis of Methacrylic Acid
  • 9.2.4 Methacrylic Acid from Biomass
  • 9.2.5 Perspectives for Development
  • 9.2.6 An Industrial Perspective for Isobutane Oxidation: Interview with Dr. Jean-Luc Dubois, Arkema
  • 9.3 Oxidation of n-Butane to Maleic Anhydride
  • 9.3.1 Introduction
  • 9.3.2 (VO)2P2O7 or VOPO4 as the Active Species? (and the Role of "Excess P")
  • 9.3.3 Recent Patent Literature
  • 9.3.4 The Role of Promoters
  • 9.3.5 The Mechanism of the Reaction
  • 9.3.6 An Industrial Perspective for n-Butane Oxidation: Interview with to Dr. Gerhard Mestl, Clariant
  • 9.3.7 An Industrial Perspective for n-Butane Oxidation: Interview with Dr. Carlotta Cortelli, Polynt SpA
  • 9.4 Oxidation and Ammoxidation of Propane to Acrylic Acid and Acrylonitrile
  • 9.4.1 Introduction
  • 9.4.2 On the Nature of Active and Selective Sites
  • 9.4.3 An Industrial Perspective for Propane Oxidation and Ammoxidation: Interview with Dr. Christian Walsdorff, BASF
  • 9.5 Oxidative Dehydrogenation (ODH) of C2-C4 Alkanes
  • 9.5.1 Introduction
  • 9.5.2 New Active Phases for Alkanes ODH
  • 9.5.3 Any Closer to Implementation?
  • 9.5.4 An Industrial Perspective for Alkanes ODH: Interview with Dr. Anne Gaffney, Idaho National Laboratory (Formerly ARCO, DuPont, Rohm and Haas, and Lummus)
  • References
  • Part II Bioinspired Alkane Functionalization
  • Chapter 10 Recent Developments of Bioinspired Approaches to Functionalization of Light Alkanes
  • 10.1 Introduction
  • 10.2 Bioinspired Oxidation of Methane
  • 10.2.1 µ-Nitrido Diiron Phthalocyanine and Porphyrin Complexes
  • 10.2.2 Fe- and Cu-Containing Zeolite Catalysts
  • 10.2.3 Bioinspired Models of Particulate MMO
  • 10.2.4 Miscellaneous Approaches
  • 10.3 Oxidation of Ethane
  • 10.4 Oxidation of Propane
  • 10.5 Final Comments
  • Acknowledgments
  • References
  • Chapter 11 Regioselectivity of Non-heme Iron Catalysts for C-H Activation
  • 11.1 Introduction
  • 11.2 The Assessment of Regioselectivity
  • 11.2.1 Commonly Used Substrates
  • 11.2.2 Substrates Used to Assess Longer-Range Impacts on Regioselectivity
  • 11.2.3 Commonly Encountered Complications in Determining the Regioselectivity of a Metal-Based Oxidant
  • 11.3 Non-heme Iron Oxidants with Strong Preferences for Weak C H Bonds
  • 11.3.1 Fe(III)-Hydroxo and -Alkoxo Species
  • 11.3.2 Fe(III)-Oxo Species
  • 11.3.3 Fe(III)-Superoxo Species
  • 11.3.4 Other Weak Non-Heme Iron Oxidants
  • 11.4 Attempts to Direct Non-Heme Iron-Catalyzed Oxidation Toward Stronger C-H Bonds
  • 11.4.1 Catalysis with Fe(II) Complexes with Unmodified TPA
  • 11.4.2 Simple Pyridylamine Complexes
  • 11.4.3 N4Py - An Illustration of the Effects of Multiple Oxidants on Site-Selectivity
  • 11.4.4 Sterically Modified TPA and Pyridylamine Ligands
  • 11.5 Directing Oxidation Through Interactions Between Functional Groups on the Ligand and Substrate: A Currently Unexplored Route for Non-heme Iron Catalysis
  • 11.6 Final Comments
  • Acknowledgments
  • References
  • Chapter 12 Imine-based Iron and Manganese Complexes as Catalysts for Alkane Functionalization
  • 12.1 Introduction
  • 12.2 Free-Radical or Radical-Free Oxidation Mechanism?
  • 12.3 Imine-Containing Complexes Competent for C-H Oxidations
  • 12.3.1 Salen-Based Catalysts
  • 12.3.2 Other Imine-Based Complexes
  • 12.3.2.1 Bidentate Ligands
  • 12.3.2.2 Tridentate Ligands
  • 12.3.2.3 Tetradentate Ligands
  • 12.3.2.4 Pentadentate Ligands
  • 12.4 Conclusions
  • Acknowledgments
  • References
  • Chapter 13 Alkane Oxidation with Biologically Inspired Nonheme Iron Catalysts Based in the Triazacyclononane Ligand Scaffold
  • 13.1 Introduction
  • 13.1.1 C-H Oxidation in Biological Systems. The Biologically Inspired Approach
  • 13.1.2 Non-Heme Iron Catalysts that Oxidize Strong C-H Bonds with Stereoretention
  • 13.2 Alkane Hydroxylation with the Fe(Pytacn) System
  • 13.2.1 The Reaction Mechanism for the C-H Hydroxylation Reaction
  • 13.2.2 Rethinking the Oxo-Hydroxo Tautomerism at Catalysts with cis-Labile Sites
  • 13.2.3 Ligand Effects in C-H Hydroxylation
  • 13.2.4 Computational Analysis on the C-H Oxidation Reactions
  • 13.2.4.1 Formation of the Active Species and Tautomerism
  • 13.2.4.2 The Mechanism of C H Hydroxylation
  • 13.2.5 Use of the [Fe(OTf)2(Mepytacn)] Catalyst in Preparative C-H Oxidation Reactions
  • 13.2.6 C-H Oxidation with a Well-Defined Fe(IV) Complex
  • 13.3 Concluding Remarks
  • Acknowledgments
  • References
  • Chapter 14 The Nature of High-Valent Oxometal Intermediates of Iron-Aminopyridine Mediated Oxidations
  • 14.1 Introduction
  • 14.2 Oxoiron Active Species of Olefin Epoxidations
  • 14.2.1 Oxoiron Active Species with High g-Factor Anisotropy Formed in the Catalyst Systems Based on Nonsubstituted Aminopyridine Iron Complexes
  • 14.2.2 Oxoiron Active Species with Low g-Factor Anisotropy Formed in the Catalyst Systems Based on Substituted Aminopyridine Iron Complexes
  • 14.3 Electronic Structure of Iron-Oxo Intermediates with High and Low g-Factor Anisotropy
  • 14.4 Switching the Electronic Structure of the Active Species by Selecting a Carboxylic Acid Additive
  • 14.5 Active Species of Olefin Epoxidations in the Catalyst Systems with Different Oxidants
  • 14.6 Iron-oxo Intermediates of C-H Oxidations
  • 14.7 Final Comments
  • Acknowledgments
  • References
  • Chapter 15 Selective Oxidation of Alkanes by Metallo-Monooxygenases and Their Nanobiomimetics
  • 15.1 Introduction
  • 15.2 Oxyfunctionalization of Hydrocarbons in Microbial Systems
  • 15.3 Metal Active Site Features of Metallo-Monooxygenases for Inert Aliphatic C H Bond Oxidation
  • 15.3.1 pMMO
  • 15.3.2 sMMO
  • 15.3.3 AlkB
  • 15.3.4 Cytochrome P450 BM3
  • 15.4 Engineering Cytochrome P450 BM3 and Alkane Hydroxylase (AlkB) for Gaseous Alkane Oxidation
  • 15.4.1 Cytochrome P450 BM3
  • 15.4.2 AlkB
  • 15.5 Homogeneous Catalysis of Oxyfunctionalization of Alkanes: Examples of Biomimetics of Metallo-Monooxygenases
  • 15.6 Heterogeneous Nanobiomimetics for Oxyfunctionalization of Normal Alkanes
  • 15.7 Final Comments
  • Acknowledgments
  • References
  • Chapter 16 Alkane Oxidation with Vanadium and Copper Catalysts
  • 16.1 Introduction
  • 16.2 Vanadium-Catalyzed Oxidation of Alkanes
  • 16.2.1 Liquid Alkanes
  • 16.2.2 Gaseous Alkanes
  • 16.2.3 Mechanism of the Vanadium-Catalyzed Peroxidative Oxidation of Alkanes
  • 16.3 Copper-Catalyzed Oxidation of Alkanes
  • 16.3.1 Mononuclear Complexes
  • 16.3.2 Polynuclear Complexes
  • 16.3.3 Copper MOF Catalysts
  • 16.3.4 Mechanism
  • 16.4 Conclusions
  • Acknowledgment
  • References
  • Part III C-B, C-C and C-N Bond Formation
  • Chapter 17 Catalytic Borylation of Methane: Combining Computational and High-Throughput Screening Approaches to Discover a New Catalyst
  • 17.1 Introduction
  • 17.2 Homogeneous Catalysts for Methane Activation and Functionalization
  • 17.2.1 Electrophilic Methane Activation and Functionalization
  • 17.2.2 Activation and Functionalization of Methane via &rmsigma
  • -Bond Metathesis
  • 17.2.3 Electrophilic Insertion of Carbenes into the C-H Bond of Methane
  • 17.2.4 Dehydrocoupling of Methane to Ethane and Ethylene with Early-Transition Metals
  • 17.3 The Inspiration Behind Iridium: Early Studies
  • 17.4 Catalytic Borylation of Aliphatic C-H Bonds
  • 17.5 Preliminary Studies on Methane Borylation Using N-Based Ligands
  • 17.6 Mechanistic Studies on the Borylation of Methane
  • 17.6.1 Experimental Studies
  • 17.6.2 Computational Studies
  • 17.7 Improving Catalyst Performance Using Phosphine Based Ligands
  • 17.8 Conclusions and Outlook
  • Acknowledgments
  • References
  • Chapter 18 Alkane Carbonylation and Carbene Insertion Reactions
  • 18.1 Introduction
  • 18.2 Carbonylation via CH Activation with Superacids or Superelectrophiles
  • 18.3 Carbonylation Reactions Catalyzed by Transition Metal Complexes
  • 18.3.1 Carbonylation Mediated by Rhodium Complexes
  • 18.3.2 Carbonylation Catalyzed by Palladium Complexes
  • 18.3.2.1 Carbonylation to Carboxylic Acids
  • 18.3.2.2 Other Carbonylation Reactions
  • 18.3.3 Carboxylation Catalyzed by Vanadium Complexes
  • 18.3.4 Carbonylation Reactions Catalyzed by Copper Complexes
  • 18.3.4.1 Hydrocarboxylation to Carboxylic Acids
  • 18.3.4.2 Other Carbonylation Reactions
  • 18.3.5 Photocatalytic Carbonylation Reactions
  • 18.4 Carbene Reactions
  • 18.5 Conclusions
  • Acknowledgments
  • References
  • Chapter 19 Catalytic Alkane Amidation and Related Reactions
  • 19.1 Introduction
  • 19.2 Amidation
  • 19.2.1 Amidation of sp3 C-H Bonds
  • 19.2.2 Amidation of C-H Bonds in Alkanes
  • 19.3 Amination
  • 19.4 Imidation
  • 19.5 Carbamation
  • 19.6 Nitration and Nitrosation
  • 19.7 Azidation
  • 19.8 Concluding Remarks
  • Acknowledgments
  • References
  • Part IV Dehydrogenation Reactions
  • Chapter 20 Oxidative and Nonoxidative Routes to Alkane Dehydrogenation
  • 20.1 Introduction
  • 20.2 Heterogeneous Catalysis
  • 20.2.1 Heterogeneous NODH
  • 20.2.2 Heterogeneous ODH
  • 20.2.3 Heterogeneous NODH vs. ODH
  • 20.3 Homogeneous NODH
  • 20.4 Homogeneous ODH
  • 20.5 Summary and Prospects
  • Acknowledgment
  • References
  • Chapter 21 Dehydrogenation of Alkanes Using Molecular Catalysts
  • 21.1 Introduction
  • 21.2 Thermochemical Dehydrogenation of Alkanes
  • 21.3 Photochemical Dehydrogenation of Alkanes
  • 21.4 Summary and Outlook
  • Acknowledgments
  • References
  • Part V Unconventional Systems
  • Chapter 22 Nontransition Metal Catalyzed Oxidation of Alkanes with Peroxides
  • 22.1 Introduction
  • 22.2 Homogeneous Hydroperoxidation of Alkanes
  • 22.2.1 Catalytic Experiments
  • 22.2.2 Experimental Kinetic Studies
  • 22.2.3 Theoretical Mechanistic Studies
  • 22.3 Hydroxylation of Methane with a Monooxygenase Zn Model
  • 22.4 Carboxylation of Alkanes
  • 22.5 Heterogeneous Oxidation of Alkanes
  • 22.6 Final Remarks
  • Acknowledgments
  • References
  • Chapter 23 Metal-Free Functionalization of Alkanes
  • 23.1 Introduction
  • 23.2 The Formation of C-C Bond
  • 23.2.1 Cross-Dehydrogenative-Coupling (CDC) Reactions
  • 23.2.2 Decarboxylative Cross-Coupling Reactions
  • 23.2.3 Conjugate Addition Reactions
  • 23.2.4 Radical Rearrangement Reactions
  • 23.2.5 Radical Cascade Reactions
  • 23.2.6 Guided Desaturation of Unactivated Aliphatics
  • 23.2.7 Difunctionalisation of 3-Substituted Coumarins
  • 23.2.8 Thermally Induced C-H Functionalization of Alkanes
  • 23.3 The Formation of C-N Bond
  • 23.4 The Formation of C-S Bond and C-Se Bond
  • 23.5 Final Comments
  • References
  • Chapter 24 Alkane Functionalization under Unconventional Conditions: in Ionic Liquid, in Supercritical CO2, and Microwave Assisted
  • 24.1 Introduction
  • 24.2 Alkane Oxidations in Ionic Liquids
  • 24.2.1 Properties of Ionic Liquids
  • 24.2.2 Ionic Liquids in Catalysis
  • 24.3 Alkane Oxidations in Supercritical CO2
  • 24.4 Microwave Promoted Oxidations
  • 24.5 Final Comments
  • Acknowledgments
  • References
  • Chapter 25 Noncovalent Interactions in Alkane Chemistry
  • 25.1 Introduction
  • 25.2 Noncovalent Organic Associates with Alkanes
  • 25.3 Noncovalent Inorganic Associates with Alkanes
  • 25.4 Final Comments
  • Acknowledgments
  • References
  • Chapter 26 Alkane Complexation
  • 26.1 Introduction and Early Work
  • 26.2 Comparison of C-H with H-H Complexation
  • 26.3 Sigma Complexation of C-H Bonds in Agostic Complexes
  • 26.4 Silane s-Complexes
  • 26.5 Transient Alkane Complexation
  • 26.6 Stable Alkane Complexes
  • 26.7 Conclusion
  • Acknowledgment
  • References
  • Chapter 27 Alkane-Related C-H Bond Activation and Functionalization of Aliphatic Amines
  • 27.1 Introduction
  • 27.2 Metal-Free Carbon-Carbon Bond Formation from Aliphatic Amines
  • 27.3 Redox Cross Dehydrogenative Coupling (CDC)
  • 27.4 Directed C-H Bond Activation
  • 27.4.1 Rhodium-Catalyzed Acylation
  • 27.4.2 Ruthenium(0)-Catalyzed Alkylation
  • 27.4.3 Ruthenium(0)-Catalyzed Arylation
  • 27.4.4 Ruthenium(II)-Catalyzed Arylation
  • 27.4.5 Palladium-Catalyzed Directed C C Bond Formation
  • 27.5 Formation of C-C Bonds Involving Metal-Catalyzed Hydrogen Transfer
  • 27.6 Miscellaneous
  • 27.6.1 Rhodium-Carbenoid Insertion into C( )-H Bonds of Aliphatic Amines
  • 27.6.2 Formation of C(2)-Substituted Imines from Cyclic Secondary Amines and Alkenes
  • 27.6.3 Formation of C( )-Substituted Enamines and Heteroaromatics Involving Hydrogen Transfer under Oxidative Conditions
  • 27.7 Final Comments and Conclusions
  • Acknowledgments
  • References
  • Index
  • Supplementary Images
  • EULA

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