Contents of Volume 1
Preface xi
1 Introduction and General Overview of Polyvalent Iodine Compounds 1
1.1 Introduction 1
1.2 Classification and Nomenclature of Polyvalent Iodine Compounds 4
1.3 Hypervalent Bonding 8
1.4 General Structural Features 10
1.5 General Principles of Reactivity 16
2 Preparation, Structure, and Properties of Polyvalent Iodine Compounds 31
2.1 Introduction 31
2.2 Iodine(III) Compounds 32
2.3 Iodine(V) Compounds 148
2.4 Iodine(VII) Compounds 164
3 Applications of Iodine(III) Reagents in Halogenations and Oxidative Functionalizations of Organic Substrates 223
3.1 Introduction 223
3.2 Fluorinations 225
3.3 Chlorinations 238
3.4 Brominations 250
3.5 Iodinations 252
3.6 Oxidation of Alcohols 258
3.7 Oxidative Functionalization of Carbonyl Compounds 262
3.8 Oxidative Functionalization of Silyl Enol Ethers 266
3.9 Oxidative Functionalization of Alkenes and Alkynes 270
3.10 Oxidations at the Benzylic or Allylic Position 278
3.11 Oxidative Functionalization of Aromatic Compounds 279
3.12 Oxidative Dearomatization of Phenols and Related Substrates 282
3.13 Oxidative Coupling of Aromatic Substrates 297
3.14 Oxidative Heterocyclizations 303
3.15 Oxidative Rearrangements 315
3.16 Radical Fragmentations and Cyclizations Initiated by [Bis(acyloxy)iodo]arenes 331
3.17 Oxidations at Nitrogen, Sulfur, and Other Heteroatoms 342
3.18 Reactions via Alkyliodine(III) Intermediates: Oxidative Deiodination of Alkyliodides 349
3.19 Transition-metal Catalyzed Oxidations 351
4 Applications of Iodine(III) Reagents in Reactions Resulting in Formation of New Câ"N , Câ"S , and Câ"Se Bonds 441
4.1 Introduction 441
4.2 Azidations 441
4.3 Amidations and Aminations 478
4.4 Thiocyanations and Arylselenations 500
References 507
Contents of Volume 2
Preface xi
5 Applications of Iodonium Salts, C-substituted Benziodoxoles, and Ylides in Organic Synthesis 531
5.1 Introduction 531
5.2 Reactions of Iodonium Salts 531
5.3 Reactions of C-substituted Benziodoxoles 556
5.4 Reactions of Iodonium Ylides 597
6 Applications of Hypervalent Iodine(V) Reagents in Organic Synthesis 659
6.1 Introduction 659
6.2 Synthetic Applications of Noncyclic and Pseudocyclic Iodylarenes 660
6.3 Synthetic Applications of 2-Iodoxybenzoic Acid 666
6.4 IBX Derivatives and Analogs 676
6.5 Dessâ"Martin Periodinane 679
7 Applications of Inorganic Polyvalent Iodine Compounds in Organic Synthesis 703
7.1 Introduction 703
7.2 Derivatives of Iodine in Oxidation State +1 703
7.3 Synthetic Applications of Inorganic Iodine(III) Reagents 705
7.4 Synthetic Applications of Inorganic Iodine(V) Reagents 706
7.5 Synthetic Applications of Inorganic Iodine(VII) Reagents 709
8 Hypervalent Iodine Catalysis 721
8.1 Introduction 721
8.2 Catalytic Cycles Based on Iodine(III) Species 722
8.3 Catalytic Cycles Based on Iodine(V) Species 748
8.4 Tandem Catalytic Systems Involving Hypervalent Iodine and Other Co-catalysts 759
8.5 Catalytic Cycles Involving Iodide Anion or Elemental Iodine as Precatalysts 764
8.6 Electrochemical Reactions Involving Hypervalent Iodine Mediators 775
9 Recyclable Hypervalent Iodine Reagents 789
9.1 Introduction 789
9.2 Polymer-supported Iodine(III) Reagents 789
9.3 Polymer-supported Iodine(V) Reagents 798
9.4 Recyclable Nonpolymeric Hypervalent Iodine(III) Reagents 803
9.5 Recyclable Nonpolymeric Hypervalent Iodine(V) Reagents 826
9.6 Recyclable Iodoarene-based Catalysts and Bifunctional Catalytic Systems 828
10 Reactions of Hypervalent Iodine Reagents in Green Solvents and Under Solvent-free Conditions 843
10.1 Introduction 843
10.2 Reactions of Hypervalent Iodine Reagents in Water 843
10.3 Reactions of Hypervalent Iodine Reagents in Recyclable Organic Solvents 850
10.4 Reactions of Hypervalent Iodine Reagents Under Solvent-free Conditions 851
11 Industrial and Biomedical Applications of Polyvalent Iodine Compounds 861
11.1 Introduction 861
11.2 Applications of Inorganic Polyvalent Iodine Derivatives 861
11.3 Applications of Hypervalent Iodine(III) Compounds as Polymerization Initiators 863
11.4 Applications of Hypervalent Iodine Compounds as Industrial Reagents 870
11.5 Application of Iodonium Salts for Fluorination in Positron Emission Tomography 871
11.6 Biological Activity of Polyvalent Iodine Compounds 883
References 887
Index 903
