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Contents
Preface 1. Introduction and General Overview of Polyvalent Iodine Compounds 1.1. Introduction
1.2. Classification and Nomenclature of Polyvalent Iodine Compounds
1.3. Hypervalent Bonding
1.4. General Structural Features
1.5. General Principles of Reactivity
2. Preparation, Structure, and Properties of Polyvalent Iodine Compounds
2.1. Introduction
2.2. Iodine(III) Compounds
2.3. Iodine(V) Compounds
2.4. Iodine(VII) Compounds
3. Applications of Iodine(III) Reagents in Halogenations and Oxidative Functionalizations of Organic Substrates
3.1. Introduction
3.2. Fluorinations
3.3. Chlorinations
3.4. Brominations
3.5. Iodinations
3.6. Oxidation of Alcohols
3.7. Oxidative Functionalization of Carbonyl Compounds
3.8. Oxidative Functionalization of Silyl Enol Ethers
3.9. Oxidative Functionalization of Alkenes and Alkynes
3.10. Oxidations at the Benzylic or Allylic Position
3.11. Oxidative Functionalization of Aromatic Compounds
3.12. Oxidative Dearomatization of Phenols and Related Substrates
3.13. Oxidative Coupling of Aromatic Substrates
3.14. Oxidative Heterocyclizations
3.15. Oxidative Rearrangements
3.16. Radical Fragmentations and Cyclizations Initiated by [Bis(acyloxy)iodo]arenes
3.17. Oxidations at Nitrogen, Sulfur, and other Heteroatoms
3.18. Reactions via Alkyliodine(III) Intermediates: Oxidative Deiodination of Alkyliodides 3.19. Transition Metal Catalyzed Oxidations
4. Applications of Iodine(III) Reagents in Reactions Resulting in Formation of New C-N, C-S, C-Se, and C-Te Bonds
4.1. Introduction
4.2. Azidations
4.3. Amidations and Aminations
4.4. Thiocyanations and Arylselenations
4.5. Reactions of Iodonium salts and C-Substituted Benziodoxoles Resulting in Formation of New C-N, C-S, and C-Se bonds
5. Applications of Iodonium Salts, C-Substituted Benziodoxoles, and Iodonium Ylides in Organic Synthesis
5.1. Introduction
5.2. Reactions of Iodonium Salts
5.3. Reactions of C-Substituted Benziodoxoles
5.4. Reactions of Iodonium Ylides
6. Applications of Hypervalent Iodine(V) Reagents in Organic Synthesis
6.1. Introduction
6.2. Synthetic Applications of Non-Cyclic and Pseudocyclic Iodylarenes Ylides
6.3. Synthetic Applications of 2-Iodoxybenzoic Acid (IBX)
6.4. IBX Derivatives and Analogs
6.5. Dess-Martin Periodinane (DMP)
7. Applications of Inorganic Polyvalent Iodine Compounds in Organic Synthesis
7.1. Introduction
7.2. Derivatives of Iodine in Oxidation State +1
7.3. Synthetic Applications of Inorganic Iodine(III) Reagents
7.4. Synthetic Applications of Inorganic Iodine(V) Reagents
7.5. Synthetic Applications of Iodine(VII) Reagents
8. Hypervalent Iodine Catalysis
8.1. Introduction
8.2. Catalytic Cycles Based on Iodine(III) Species
8.3. Catalytic Cycles Based on Iodine(V) Species
8.4. Tandem Catalytic Systems Involving Hypervalent Iodine and other co-Catalysts
8.5. Catalytic Cycles Involving Iodide Anion or Elemental Iodine as Precatalysts
8.6. Electrochemical Reactions Involving Hypervalent Iodine Mediators
9. Recyclable Hypervalent Iodine Reagents
9.1. Introduction
9.2. Polymer-Supported Iodine(III) Reagents
9.3. Polymer-Supported Iodine(V) Reagents
9.4. Recyclable Nonpolymeric Hypervalent Iodine(III) Reagents
9.5. Recyclable Nonpolymeric Hypervalent Iodine(V) Reagents
9.6. Recyclable Iodoarene-Based Catalysts and Bifunctional Catalytic Systems
10. Reactions of Hypervalent Iodine Reagents in Green Solvents and under Solvent-Free Conditions
10.1. Introduction
10.2. Reactions of Hypervalent Iodine Reagents in Water
10.3. Reactions of Hypervalent Iodine Reagents in Recyclable Organic Solvents
10.4. Reactions of Hypervalent Iodine Reagents Under Solvent-Free Conditions
11. Industrial and Biomedical Applications of Polyvalent Iodine Compounds
11.1. Introduction
11.2. Applications of Inorganic Polyvalent Iodine Derivatives
11.3. Applications of Hypervalent Iodine(III) Compounds as Polymerization Initiators
11.4 Applications of Hypervalent Iodine Compounds as Industrial Reagents
11.5. Application of Iodonium Salts for Fluoridation in Positron Emission Tomography (PET)
11.6. Biological Activity of Polyvalent Iodine Compounds
12. Index
