Modern Synthesis Processes and Reactivity of Fluorinated Compounds

Modern Synthesis Processes and Reactivity of Fluorinated Compounds

Progress in Fluorine Science

1st Edition - November 4, 2016

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  • Editors: Henri Groult, Frederic Leroux, Alain Tressaud
  • eBook ISBN: 9780128037904
  • Paperback ISBN: 9780128037409

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Modern Synthesis Processes and Reactivity of Fluorinated Compounds focuses on the exceptional character of fluorine and fluorinated compounds. This comprehensive work explores examples taken from all classes of fluorine chemistry and illustrates the extreme reactivity of fluorinating media and the peculiar synthesis routes to fluorinated materials. The book provides advanced and updated information on the latest synthesis routes to fluorocompounds and the involved reaction mechanisms. Special attention is given to the unique reactivity of fluorine and fluorinated media, along with the correlation of those properties to valuable applications of fluorinated compounds.

Key Features

  • Contains quality content edited, and contributed, by leading scholars in the field
  • Presents applied guidance on the preparation of original fluorinated compounds, potentially transferable from the lab scale to industrial applications
  • Provides practical synthesis information for a wide audience interested in fluorine compounds in many branches of chemistry, materials science, and physics


Inorganic chemistry researchers in industry/academia

Table of Contents

  • Chapter One. The Cosmic Origin of Fluorine: An Astronomer's View on Fluorine Synthesis

    • 1. The Cosmic Origin of the Elements
    • 2. The Cosmic Origin of Fluorine

    Chapter Two. The Fluorine Atom in Health Care and Agrochemical Applications: A Contribution to Life Science

    • 1. Introduction
    • 2. Methods to Introduce Fluorine Into Organic Molecules
    • 3. Use of Trifluoromethyl Group in Pharmaceuticals and Agrochemistry
    • 4. Use of Difluoromethyl Group in Pharmaceuticals and Agrochemistry

    3. Industrial Syntheses of Hydrohaloolefins and Related Products

    • 1. Introduction
    • 2. Hydrofluoroolefins
    • 3. Other Hydrofluoroolefins
    • 4. Hydrochlorofluoroolefins
    • 5. Conclusion

    4. Electrochemical Fluorination: A Powerful Tool for the Preparation of Organofluorine Compounds

    • 1. Introduction and Historical Overview
    • 2. Technical Aspects of the Electrochemical Fluorination (Simons Process)
    • 3. Mechanism of Electrochemical Fluorination (Simons Process)
    • 4. Carbon Chain Isomerization During Electrochemical Fluorination (Simons Process)
    • 5. Electrochemical Fluorination of the Elementorganic Compounds

    5. Once Upon a Time Was the Langlois' Reagent: A “Sleeping Beauty”

    • 1. Introduction
    • 2. Origin of the Trifluoromethanesulfinate Salts and Their First Uses
    • 3. Rebirth of the “Langlois' Reagent”
    • 4. Conclusions

    6. Toward CF3S Group: From Trifluoromethylation of Sulfides to Direct Trifluoromethylthiolation

    • 1. Introduction
    • 2. Indirect Methods
    • 3. Direct Preparation: Trifluoromethylthiolation
    • 4. Conclusions

    7. Nucleophilic Di- and Trifluoromethylation of CO and CN Bonds

    • 1. Introduction
    • 2. Trifluoromethylation Reactions
    • 3. Difluoromethylation Reactions
    • 4. Conclusion

    8. Oxidative Trifluoromethylation and Trifluoromethylthiolation

    • 1. Introduction
    • 2. Oxidative Trifluoromethylation
    • 3. Oxidative Trifluoromethylthiolation
    • 4. Other Oxidative Fluoroalkylations
    • 5. Conclusion

    9. Catalytic Enantioselective Fluorination

    • 1. Introduction
    • 2. Electrophilic Fluorination Methods
    • 3. Nucleophilic Fluorination
    • 4. Conclusions and Outlook

    10. Development of Electrophilic Trifluoromethylating Reagents

    • 1. Introduction
    • 2. Historical Background
    • 3. Electrophilic Trifluoromethylating Reagents
    • 4. Conclusion

    11. New Nucleophilic Fluoroalkylations

    • 1. Introduction
    • 2. Nucleophilic Trifluoroalkylation Reactions
    • 3. Difluoroalkylation Reactions
    • 4. Nucleophilic Monofluoroalkylation Reactions

    12. Continuous Flow Selective Direct Fluorination Using Fluorine Gas

    • 1. Introduction
    • 2. Continuous Flow Processes Using Fluorine Gas
    • 3. Selective Direct Fluorination by Continuous Flow Processes
    • 4. Conclusions

    13. Synthesis of Fluorinated Nitrogen-Containing Compounds Through Superelectrophilic Activation in Superacid HF/SbF5

    • 1. Introduction
    • 2. Hydrofluorination of CC Double Bond in Superacid HF/SbF5
    • 3. Hydrofluorination of CC Triple Bond in Superacid HF/SbF5
    • 4. Cyclization and Cyclization/Fluorination in Superacid HF/SbF5
    • 5. Halofluorination of Unsaturated Nitrogen-Containing Substrates in Superacid HF/SbF5
    • 6. Exploitation of Superacid-Catalyzed Hydrofluorination of Unsaturated Amines in Superacid HF/SbF5 for Bioorganic Studies
    • 7. Conclusion

    14. Visible Light–Induced (Per)fluoroalkylation by Photoredox Catalysis

    • 1. Introduction
    • 2. (Per)fluoroalkylation Reactions Using Photoredox-Induced Monofunctionalization
    • 3. (Per)fluoroalkylation Using Photoredox-Induced Difunctionalization of Unsaturated Systems
    • 4. Conclusion

    15. Synthesis of Side Chain Fluorinated Amino Acids and Their Effects on the Properties of Peptides and Proteins

    • 1. Introduction
    • 2. Synthesis of Fluorinated Aliphatic α-Amino Acids
    • 3. Fluorinated Amino Acids in Peptides
    • 4. Summary and Prospects

    16. Ionic Liquids and Polymers for Battery and Fuel Cells

    • 1. Introduction
    • 2. Fluorinated Compounds in Lithium-Ion Battery
    • 3. Aromatic Ionomers Bearing Perfluorosulfonic Acid Side Chains

    17. Strategic Incorporation of Fluorine for Drug Discovery and Development

    • 1. Introduction
    • 2. Case Study 1: Incorporation of Fluorine Increased the Binding Affinity of a Drug to Its Protein Target
    • 3. Case Study 2: Incorporation of Fluorine Increased Potency In Vitro
    • 4. Case Study 3: Incorporation of Fluorine Increased Both In Vitro and In Vivo Potency
    • 5. Case Study 4: Use of a 18F-Positron Emission Tomographic Tracer Replaced an Expensive 11C-Positron Emission Tomographic Tracer for Practical Diagnosis of Alzheimer Disease
    • 6. Conclusions

    18. Telomerization Reaction of 3,3,3-Trifluoropropene

    • 1. Introduction
    • 2. Telomerization of 3,3,3-Trifluoropropene
    • 3. Synthesis of Surfactants Based on 3,3,3-Trifluoropropene
    • 4. Conclusions

    19. High Oxidation States in Transition Metal Fluorides

    • 1. Introduction
    • 2. 3d Elements
    • 3. 4d Metals
    • 4. 5d Elements
    • 5. Outlook

    20. Photochemical Syntheses of Fluorides in Liquid Anhydrous Hydrogen Fluoride

    • 1. Introduction
    • 2. Requirements of Photochemical Syntheses With Elemental F2 in Anhydrous HF
    • 3. Reaction Mechanism
    • 4. Examples of F2 Fluorinations in Liquid Anhydrous HF at Ambient Temperature
    • 5. Conclusions

    21. Sol–Gel Synthesis of Metal Fluorides: Reactivity and Mechanisms

    • 1. Introduction
    • 2. The Principle Chemistry of the Fluorolytic Sol–Gel Synthesis
    • 3. Mechanistic Aspects of Fluorolytic Sol–Gel Synthesis as Seen by Nuclear Magnetic Resonance Methods
    • 4. Applications

    22. Solution-Based Synthesis of Nano-Sized TiO2 Anatase in Fluorinating Media

    • 1. Introduction
    • 2. General Interests of Fluorinating Media
    • 3. Evidences for the Stabilization of Fluoride in Anatase Featuring Cationic Vacancies
    • 4. Conclusion

    23. Ionic Liquid Materials Based on Fluoroanions

    • 1. Introduction
    • 2. Syntheses and Structures of Ionic Liquids Based on Fluorohydrogenate Anions
    • 3. Properties of Ionic Liquids Based on Fluorohydrogenate Anions
    • 4. Syntheses of Ionic Liquids Based on Fluorocomplex and Oxofluorocomplex Anions
    • 5. Structures and Properties of Ionic Liquids Based on Fluorocomplex Anions
    • 6. Conclusions

    24. Reactivity of Surface Fluorinated TiO2 and TiAl Particles

    • 1. Surface Fluorination of TiO2 Particles
    • 2. Surface Fluorination of TiAl Alloy Particles
    • 3. Conclusions

    25. Chemical and Electrochemical Stability of Copper in Molten KF-2HF

    • 1. Introduction
    • 2. Experimental Section
    • 3. Results
    • 4. Conclusions

Product details

  • No. of pages: 760
  • Language: English
  • Copyright: © Elsevier 2016
  • Published: November 4, 2016
  • Imprint: Elsevier
  • eBook ISBN: 9780128037904
  • Paperback ISBN: 9780128037409

About the Editors

Henri Groult

Henri Groult is Director of Research of CNRS-UPMC-ESPCI UMR 7612, University of Pierre and Marie Curie (Paris 6) in France. He has devoted his research life to fluorine chemistry, electrochemistry, and molten salt chemistry. His main research subjects are electrolytic production of fluorine gas, fluorine compounds for primary and secondary lithium batteries, and electrochemical properties of molten fluorides and chlorides. He has obtained interesting results on fluorine evolution reaction on carbon electrodes, discharge behavior of carbon-fluorine compounds, charge/discharge characteristics of metal fluorides, and electrochemical properties of molten salts. On these subjects, he published more than 100 papers and 7 books. His activity has played an important role in fluorine chemistry in France. He has served as Director of the French Network of Fluorine, Chairman of the 17th European Symposium on Fluorine Chemistry (Paris, July 2013), and Editorial board of J. Fluorine Chemistry.

Affiliations and Expertise

University of Pierre and Marie Curie, Paris, France

Frederic Leroux

Frederic Leroux is CNRS Research Director at the University of Strasbourg. He is Director of the joint CNRS-Bayer laboratory of organofluorine chemistry and director of the molecular chemistry department (UMR CNRS 7042-LIMA) at the European School of Chemistry, Polymers and Material Sciences (ECPM). His research is published in >110 peer-reviewed papers, 18 patents, 8 book chapters and presented by invitation at >100 (inter)national conferences. He is Fellow of the Royal Society of Chemistry (FRSC) and member of the European Academy of Sciences and Arts. He is also a member of the International Scientific Committee of the Moissan Prize (Fluorine Chemistry) and Director of the French Fluorine Network. His scientific interest covers various fields, based on a fruitful interplay of several objectives (a) the synthesis of biologically relevant molecules, (b) asymmetric methodologies using organic and organometallic chemistry, (c) organofluorine chemistry and (d) application of the objectives to industrial problems, which led to strong industrial collaborations.

Affiliations and Expertise

Université de Strasbourg, Université de Haute-Alsace, CNRS, UMR 7042-LIMA, F-67000 Strasbourg, France

Alain Tressaud

Alain Tressaud
Alain Tressaud is Emeritus Research Director at ICMCB-CNRS, Bordeaux University. He is President of the European Academy of Science in Brussels and member of several European academies. He founded and chaired the French Network on Fluorine Chemistry, sponsored by CNRS, until 2008. He has received several awards, including the CEA Award of French Academy of Sciences (2008), the Fluorine Award of the American Chemical Society (2011), and the International Henri Moissan Prize (2013). His scientific interest covers various fields, including synthesis, physical chemical characterizations, applications in fluorine chemistry, solid state chemistry, and materials sciences. His work also deals with surface modification of materials and intercalation chemistry. Professor Tressaud’s scientific production includes more than 360 papers in international journals, 20 book chapter contributions, and 12 internationalized patents. He has also edited several books in his role as editor-in-chief of the series “Advances in Fluorine Science” (2006) and “Progress in Fluorine Science” (2016) with Elsevier.

Affiliations and Expertise

ICMCB-CNRS University of Bordeaux, Pessac Cedex, France

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