Note: Intro -- COMPREHENSIVE ORGANIC REACTIONS IN AQUEOUS MEDIA -- CONTENTS -- PREFACE TO THE SECOND EDITION -- 1 INTRODUCTION -- 1.1 The Structure and Forms of Water -- 1.2 Properties of Water -- 1.3 Solvation -- 1.4 Hydrophobic Effect -- 1.5 Salt Effect -- 1.6 Water Under Extreme Conditions -- References -- 2 ALKANES -- 2.1 Oxygenation of Alkanes -- 2.2 Halogenation of Alkanes -- 2.3 Formation of Carbon-Carbon Bonds -- 2.4 D/H Exchange of Alkanes in Water -- References -- 3 ALKENES -- 3.1 Reduction -- 3.1.1 Hydrogenation -- 3.2 Electrophilic Additions -- 3.2.1 Reaction with Halogen -- 3.2.2 Reaction with Hydrogen Halides -- 3.2.3 Addition of Water -- 3.2.4 Oxymercuration/Oxymetalation -- 3.2.5 Epoxidation -- 3.2.6 Dihydroxylation and Hydroxylamination -- 3.2.7 Wacker's Oxidation -- 3.2.8 Oxidative C=C Bond Cleavage -- 3.2.9 C-C Bond Formations -- 3.3 Radical Reactions of Alkenes -- 3.3.1 Radical Polymerization of Alkenes -- 3.3.2 Radical Additions -- 3.3.3 Radical Cyclization -- 3.4 Carbene Reactions -- 3.4.1 The Generation of Carbenes in Aqueous Medium -- 3.4.2 The Stability of Carbenes -- 3.4.3 The Reaction of Carbenes with Alkenes in Aqueous Medium -- 3.5 Alkene Isomerization -- 3.6 Transition-Metal Catalyzed C-C Formation Reactions -- 3.6.1 Polymerizations -- 3.6.2 Heck Reactions and Related Vinylation/Arylation -- 3.6.3 Hydrovinylation -- 3.6.4 Reaction with Arenes -- 3.6.5 Hydroformylation -- 3.6.6 Reaction with Alkynes -- 3.6.7 Carbonylation -- 3.6.8 Cycloaddition Reactions of Alkenes -- 3.7 Olefin Metathesis -- 3.7.1 Ring-Opening Metathesis Polymerization (ROMP) -- 3.7.2 Ring-Closing Metathesis (RCM) -- 3.8 Reaction of Allylic C-H Bond -- 3.8.1 Allylic Oxidation -- 3.8.2 C-C Bond Formations -- References -- 4 ALKYNES -- 4.1 Reaction of Terminal Alkynes -- 4.1.1 Alkyne Oxidative Dimerization -- 4.1.2 Alkyne-Alkyne Addition. , 4.1.3 Reaction of Alkynes with Organic Halides -- 4.1.4 Reaction of Alkynes with Carbonyl Compounds -- 4.1.5 Reaction of Alkynes with C=N Compounds -- 4.1.6 Conjugate Addition with Terminal Alkynes -- 4.2 Additions of C≡C bonds -- 4.2.1 Reduction -- 4.2.2 Addition of Water -- 4.2.3 Addition of Alcohols and Amines -- 4.2.4 Hydrosilation and Hydrometalations -- 4.2.5 Addition of Aryls -- 4.2.6 Carbonylation of Internal Alkynes -- 4.2.7 Other Additions to Alkynes -- 4.3 Transition-Metal Catalyzed Cycloadditions -- 4.3.1 Pauson-Khand-Type Reactions -- 4.3.2 [2 + 2 + 2] Cyclotrimerization -- 4.3.3 [2 + 2 + 2] Alkyne-Nitrile Cyclotrimerization -- 4.3.4 [3 + 2] 1,3-Dipolar Cycloaddition -- 4.3.5 [4 + 2] Cycloaddition -- 4.3.6 [5 + 2] Cycloaddition -- 4.3.7 Other Cycloadditions -- 4.4 Other Reactions -- References -- 5 ALCOHOLS, PHENOLS, ETHERS, THIOLS, AND THIOETHERS -- 5.1 Oxidation of Alcohols -- 5.1.1 Diol Cleavage -- 5.2 Substitutions/Elimination -- 5.3 Addition of Alcohols, Phenols, and Thiols to Alkene and Alkyne Bonds -- 5.4 Addition of Alcohols to C=O Bonds: Esterification and Acetal Formations -- 5.5 Reaction of Ethers and Cyclic Ethers -- 5.5.1 Ethers and Cyclic Ethers -- 5.5.2 Reactions of Epoxides in Water and "Click Chemistry" -- 5.6 Reaction of Sulfur Compounds -- 5.6.1 Oxidation of Thiols and Thioethers -- 5.6.2 Reduction of Disulfides -- 5.6.3 Native Chemical Ligation for Peptide Synthesis -- 5.6.4 Other Reactions -- References -- 6 ORGANIC HALIDES -- 6.1 General -- 6.2 Reduction -- 6.3 Elimination Reactions -- 6.4 Nucleophilic Substitutions -- 6.4.1 Substituted by Heteroatoms -- 6.4.2 Carbon-Carbon Bond Formations -- 6.5 Reductive Coupling -- 6.5.1 Wurtz-Type Coupling -- 6.5.2 Ullmann-Type Coupling and Related Reactions -- 6.6 Carbonylation of Organic Halides -- 6.6.1 Carbonylation of Alkyl Halides. , 6.6.2 Carbonylation of Allylic and Benzylic Halides -- 6.6.3 Carbonylation of Aryl Halides -- 6.7 Transition-Metal Catalyzed Coupling Reactions -- 6.7.1 The Heck Coupling -- 6.7.2 The Suzuki Coupling -- 6.7.3 The Stille Coupling -- 6.7.4 Other Transition-Metal Catalyzed Couplings -- References -- 7 AROMATIC COMPOUNDS -- 7.1 General -- 7.2 Substitution Reactions -- 7.2.1 Electrophilic Substitutions -- 7.2.2 Friedel-Crafts C-C Bond Formations -- 7.2.3 Other Substitution Reactions -- 7.3 Oxidation Reactions -- 7.3.1 Simple Oxidation -- 7.3.2 Oxidative Coupling -- 7.4 Reductions -- References -- 8 ALDEHDYE AND KETONES -- 8.1 Reduction -- 8.1.1 Hydrogenation -- 8.1.2 Other Reductions -- 8.2 Oxidation -- 8.3 Nucleophilic Addition: C-C Bond Formation -- 8.3.1 Allylation -- 8.3.2 Propargylation -- 8.3.3 Cyclopentadienylation -- 8.3.4 Benzylation -- 8.3.5 Arylation/Vinylation -- 8.3.6 Alkynylation -- 8.3.7 Alkylation -- 8.3.8 Reformatsky-Type Reaction -- 8.3.9 Direct Aldol Reaction -- 8.3.10 Mukaiyama Aldol Reaction -- 8.3.11 Hydrogen Cyanide Addition -- 8.3.12 Wittig Reactions -- 8.4 Pinacol Coupling -- 8.5 Other Reactions (Halogenation and Oxidation of α-H) -- References -- 9 CARBOXYLIC ACIDS AND DERIVATIVES -- 9.1 General -- 9.1.1 Reaction of α-Hydrogen -- 9.1.2 Reduction -- 9.2 Carboxylic Acids -- 9.2.1 Esterification/Amidation -- 9.2.2 Decarboxylation -- 9.3 Carboxylic Acid Derivatives -- 9.3.1 Esters and Thiol Esters -- 9.3.2 Acid Halides and Anhydrides -- 9.3.3 Amides -- 9.3.4 Nitriles -- References -- 10 CONJUGATED CARBONYL COMPOUNDS -- 10.1 Reduction -- 10.1.1 Hydrogenation -- 10.1.2 Asymmetric Hydrogenation -- 10.1.3 Reduction by Other Methods -- 10.2 Epoxidation, Dihydroxylation, Hydroxyamination -- 10.3 Conjugate Addition: Heteroatom -- 10.4 C-C Bond Formation -- 10.4.1 Addition of Hydrogen Cyanide -- 10.4.2 Addition of α-Carbonyl Compounds. , 10.4.3 Addition of Allyl Groups -- 10.4.4 Addition of Alkyl Groups -- 10.4.5 Addition of Vinyl and Aryl Groups -- 10.4.6 Addition of Alkynyl Groups -- 10.4.7 Other Conjugate Additions -- 10.5 Other Reactions -- 10.5.1 Reductive Coupling -- 10.5.2 Baylis-Hillman Reactions -- 10.5.3 γ-Addition of Alkynoates -- References -- 11 NITROGEN COMPOUNDS -- 11.1 Amines -- 11.1.1 Alkylation -- 11.1.2 Diazotization and Nitrosation -- 11.1.3 Oxidation -- 11.1.4 Reaction with Carbonyl Compounds -- 11.2 Imines -- 11.2.1 Reductions -- 11.2.2 Nucleophilic Additions -- 11.2.3 Reductive Coupling -- 11.3 Diazo Compounds -- 11.3.1 Substitution -- 11.3.2 Reduction -- 11.3.3 Cyclopropanation -- 11.3.4 Coupling Reaction -- 11.4 Azides -- 11.4.1 Substitution -- 11.4.2 Click Chemistry -- 11.5 Nitro Compounds -- References -- 12 PERICYCLIC REACTIONS -- 12.1 Introduction -- 12.2 Diels-Alder Reactions -- 12.2.1 Lewis-Acid Catalysis -- 12.2.2 Asymmetric Diels-Alder Reactions -- 12.2.3 Theoretical and Mechanistic Studies -- 12.2.4 Synthetic Applications -- 12.2.5 Hetero-Diels-Alder Reactions -- 12.2.6 Asymmetric Hetero-Diels-Alder Reactions -- 12.2.7 Other Cyclization Reactions -- 12.3 Sigmatropic Rearrangements -- 12.3.1 Claisen Rearrangements -- 12.3.2 Cope Rearrangements -- 12.4 Photochemical Cycloaddition Reactions -- References -- INDEX.

Note: Intro -- Modern Alkyne Chemistry -- Contents -- List of Contributors -- Preface -- Chapter 1 Introduction -- 1.1 History of Alkynes -- 1.2 Structure and Properties of Alkynes -- 1.3 Classical Reactions of Alkynes -- 1.4 Modern Reactions -- 1.5 Conclusion -- References -- Part I Catalytic Isomerization of Alkynes -- Chapter 2 Redox Isomerization of Propargyl Alcohols to Enones -- 2.1 Introduction -- 2.2 Base Catalysis -- 2.3 Ru Catalyzed -- 2.4 Rh Catalysis -- 2.5 Palladium Catalysis -- 2.6 Miscellaneous -- 2.7 Conclusions -- References -- Chapter 3 Carbophilic Cycloisomerization Reactions of Enynes and Domino Processes -- 3.1 Introduction and Reactivity Principles -- 3.1.1 The Reactivity of Carbophilic Lewis Acids in the Presence of Enyne Substrates -- 3.2 Skeletal Rearrangement Reactions in the Absence of Nucleophiles -- 3.2.1 Synthesis of Dienes (1,3- and 1,4-Dienes) -- 3.2.2 Cycloisomerization Reactions Involving Activated Alkene Partners: Conia-Ene Reaction and Related Transformations -- 3.2.3 Formation of Bicyclic Derivatives -- 3.2.3.1 Formation of Bicyclopropanes -- 3.2.3.2 Formation of Bicyclobutenes -- 3.2.3.3 Formation of Larger Rings via Cycloisomerization-Rearrangements -- 3.3 Enyne Domino Processes -- 3.3.1 Domino Enyne Cycloisomerization-Nucleophile Addition Reactions -- 3.3.1.1 Oxygen and Nitrogen Nucleophiles -- 3.3.1.2 Carbon Nucleophiles -- 3.4 Conclusion -- References -- Chapter 4 Alkyne Metathesis in Organic Synthesis -- 4.1 Introduction -- 4.2 Mechanistic Background and Classical Catalyst Systems -- 4.3 State-of-the-Art Catalysts -- 4.4 Basic Reaction Formats and Substrate Scope -- 4.5 Selected Applications -- 4.5.1 Dehydrohomoancepsenolide -- 4.5.2 Olfactory Macrolides -- 4.5.3 Haliclonacyclamine C -- 4.5.4 Hybridalactone -- 4.5.5 Cruentaren A -- 4.5.6 The Tubulin-Inhibitor WF-1360F -- 4.5.7 Neurymenolide A. , 4.5.8 Leiodermatolide -- 4.5.9 Tulearin C -- 4.5.10 The Antibiotic A26771B -- 4.5.11 Lactimidomycin -- 4.5.12 Citreofuran -- 4.5.13 Polycavernoside -- 4.5.14 Amphidinolide F -- 4.5.15 Spirastrellolide F Methyl Ester -- 4.6 Conclusions -- References -- Part II Catalytic Cycloaddition Reactions -- Chapter 5 Alkyne-Azide Reactions -- 5.1 Introduction -- 5.2 Reviews on Cu-Catalyzed Azide-Alkyne Cycloaddition -- 5.3 Mechanistic Considerations on the Cu(1) Catalysis -- 5.4 The Substrates for CuAAC -- 5.5 The Environment -- 5.6 Modified 1,2,3-Triazoles and CuAAC Side Reactions -- 5.6.1 Oxidative Couplings of Cu(1)-Triazole Complexes -- 5.6.2 Reactions in the 5-Position of Triazoles -- 5.6.3 Side Reactions due to Substrate Instability -- 5.7 The Catalyst -- 5.7.1 Recent Ligands and their Influence on Cu(1) Catalysis -- 5.7.2 Catalyst Structure-Activity Relationship -- 5.7.3 In Situ Generated CuAAC: Electro-, Photo-, and Self-Induced ``Click'' -- 5.8 Optimizing Conditions for CuAAC Reactions -- 5.9 CuAAC in Biological Applications -- 5.10 Biocompatibility of the CuAAC Reaction -- References -- Chapter 6 Catalytic Cycloaddition Reactions -- 6.1 Introduction -- 6.2 (2+2) Cycloaddition -- 6.3 (3+2) and (2+1) Cycloaddition -- 6.4 (4+2) Cycloaddition -- 6.5 (5+1) and (4+1) Cycloadditions -- 6.6 (5+2) Cycloaddition -- 6.7 (6+2) Cycloaddition -- 6.8 (2+2+1) Cycloaddition -- 6.9 (2+2+2) Cycloaddition -- 6.10 (3+2+1) Cycloaddition -- 6.11 (3+2+2) Cycloaddition -- 6.12 (4+2+1) and (4+2+2) Cycloaddition -- 6.13 (4+3+2) Cycloaddition -- 6.14 (5+2+1) and (5+1+2+1) Cycloadditions -- 6.15 (2+2+1+1) and (2+2+2+1) Cycloadditions -- 6.16 (2+2+2+2) Cycloaddition -- 6.17 Conclusions -- References -- Part III Catalytic Nucleophilic Additions and Substitutions -- Chapter 7 Catalytic Conjugate Additions of Alkynes -- 7.1 Introduction -- 7.2 Metal Alkynylides as Nucleophiles. , 7.2.1 Conjugate Addition of Metal Alkynylides -- 7.2.1.1 Conjugate Addition of Metal Alkynylides to s-cis α,β-Enones -- 7.2.1.2 Conjugate Addition of Metal Alkynylides with a Catalytic Promoter -- 7.2.1.3 Conjugate Addition of Metal Alkynylides with Stoichiometric Promoters -- 7.2.2 Enantioselective Conjugate Addition of Metal Alkynylides -- 7.2.2.1 Use of a Stoichiometric Amount of Chiral Sources -- 7.2.2.2 Catalytic Enantioselective Conjugate Addition of Metal Alkynylides -- 7.3 Direct Use of Terminal Alkynes as Pronucleophiles -- 7.3.1 Direct Catalytic Conjugate Addition of Terminal Alkynes -- 7.3.1.1 Introduction -- 7.3.1.2 Addition to Vinyl Ketones and Acrylates -- 7.3.1.3 Addition to β-Substituted α,β-Enones -- 7.3.2 Enantioselective Direct Catalytic Conjugate Addition of Terminal Alkynes -- 7.4 Summary and Conclusions -- References -- Chapter 8 Catalytic Enantioselective Addition of Terminal Alkynes to Carbonyls -- 8.1 Introduction -- 8.2 Metallation of Terminal Alkynes: Formation of Alkynyl Nucleophiles -- 8.2.1 Deprotonation of Terminal Alkynes -- 8.2.2 Oxidative Insertion and Ligand Exchange: Formal Metallation of Terminal Alkynes -- 8.3 Ligand-Catalyzed Alkyne Additions with Stoichiometric Quantities of Metal -- 8.3.1 Addition of Alkynylzinc Nucleophiles to Aldehydes, Ketones, and Imines -- 8.3.2 Titanium-Catalyzed Alkynylation of Aldehydes and Ketones -- 8.3.3 Asymmetric Boron-Catalyzed Alkyne Additions to Aldehydes -- 8.4 Alkyne Additions with Catalytic Amounts of Metal -- 8.4.1 Asymmetric Alkyne Additions to Aldehydes and Ketones Catalyzed by Zinc Salts -- 8.4.2 Indium-Catalyzed Alkyne Additions to Aldehydes -- 8.4.3 Chromium-Catalyzed Alkynylation of Aldehydes with Haloacetylenes -- 8.4.4 Copper-Catalyzed Alkynylation of Aldehydes and Trifluoromethyl Ketones. , 8.4.5 Palladium-Catalyzed Additions to α,β-Unsaturated Carbonyls and Trifluoropyruvate -- 8.4.6 Enantioselective Ruthenium-Catalyzed Alkynylation of Aldehydes -- 8.4.7 Rhodium-Catalyzed Alkynylation of α-Ketoesters -- 8.5 Concluding Remarks -- References -- Chapter 9 Catalytic Nucleophilic Addition of Alkynes to Imines: The A3 (Aldehyde-Alkyne-Amine) Coupling -- 9.1 A3 Couplings Involving Primary Amines -- 9.2 A3 Couplings Involving Secondary Amines -- 9.3 Alkyne Additions with Reusable Catalysts -- 9.4 Asymmetric Alkyne Addition Reactions -- 9.4.1 Asymmetric A3-Type Couplings with Primary Amines -- 9.4.2 Asymmetric A3-Type Couplings with Secondary Amines -- 9.5 Alkyne Additions to Imines in Tandem Reactions -- 9.5.1 A3 Coupling with Tandem Cycloisomerizations Involving the Alkyne Triple Bond -- 9.5.2 Tandem Processes Involving Other Transformations of the Alkyne Triple Bond -- 9.5.3 Tandem Processes Involving Decarboxylations -- 9.5.4 Tandem Processes Involving Both the Amine and the Alkyne -- 9.6 Conclusion -- References -- Chapter 10 The Sonogashira Reaction -- 10.1 Introduction -- 10.2 Palladium-Phosphorous Catalysts -- 10.2.1 Unsupported Palladium-Phosphorous Catalysts -- 10.2.1.1 Copper-Cocatalyzed Reactions -- 10.2.1.2 Copper-Free Reactions -- 10.2.2 Supported Palladium-Phosphorous Catalysts -- 10.2.2.1 Copper-Cocatalyzed Reactions -- 10.2.2.2 Copper-Free Reactions -- 10.3 Palladium-Nitrogen Catalysts -- 10.3.1 Unsupported Palladium-Nitrogen Catalysts -- 10.3.2 Supported Palladium-Nitrogen Catalysts -- 10.4 N-Heterocyclic Carbene (NHC)-Palladium Catalysts -- 10.4.1 Unsupported NHC-Palladium Catalysts -- 10.4.2 Supported NHC-Palladium Catalysts -- 10.5 Palladacycles as Catalysts -- 10.5.1 Unsupported Palladacycles as Catalysts -- 10.5.2 Supported Palladacycles as Catalysts -- 10.6 Ligand-Free Palladium Salts as Catalysts. , 10.6.1 Unsupported Ligand-Free Palladium Salts as Catalysts -- 10.6.2 Supported Ligand-Free Palladium Salts as Catalysts -- 10.7 Palladium Nanoparticles as Catalysts -- 10.7.1 Unimmobilized Palladium Nanoparticles as Catalysts -- 10.7.2 Immobilized Palladium Nanoparticles as Catalysts -- 10.7.2.1 Copper-Cocatalyzed Reactions -- 10.7.2.2 Copper-Free Reactions -- 10.8 Non-Palladium-Based Catalysts -- 10.9 Mechanistic Considerations -- 10.10 Summary and Conclusions -- References -- Part IV Other Reactions -- Chapter 11 Catalytic Dimerization of Alkynes -- 11.1 Introduction -- 11.2 Dimerization of Alkynes Catalyzed by Iron, Ruthenium, and Osmium Complexes -- 11.2.1 Homo-Coupling of Terminal Alkynes -- 11.2.2 Cross-Dimerization of Alkynes -- 11.3 Dimerization of Alkynes Catalyzed by Cobalt, Rhodium, and Iridium Complexes -- 11.3.1 Homo-Coupling of Terminal Alkynes -- 11.3.2 Cross-Dimerization of Alkynes -- 11.4 Dimerization of Alkynes Catalyzed by Nickel, Palladium, and Platinum Complexes -- 11.4.1 Homo-Coupling of Terminal Alkynes -- 11.4.2 Cross-Dimerization of Alkynes -- 11.5 Dimerization of Alkynes Catalyzed by Group 3, Lanthanide, and Actinide Complexes -- 11.6 Dimerization of Alkynes Catalyzed by Titanium, Zirconium, and Hafnium Complexes -- 11.7 Dimerization of Alkynes Catalyzed by Other Compounds -- 11.8 Summary and Conclusions -- Acknowledgments -- References -- Chapter 12 The Oxidative Dimerization of Acetylenes and Related Reactions: Synthesis and Applications of Conjugated 1,3-Diynes -- 12.1 Introduction -- 12.2 Syntheses of Conjugated 1,3-Diynes -- 12.3 Scope and Limitation of the Alkyne Dimerization Reaction -- 12.3.1 Choice of Copper Salt -- 12.3.2 Choice of Solvent -- 12.3.3 Substituents on the Alkyne and Basic Additives -- 12.3.4 Additional Metals -- 12.4 Scope and Limitation of Copper-Catalyzed Hetero-Coupling Reactions. , 12.5 The Cadiot-Chodkiewicz Reaction.

Note: Intro -- Title Page -- Preface -- Contents -- CHAPTER 1 The Evolution of the Concept of Cross-Dehydrogenative- Coupling Reactions SIMON A. GIRARD, THOMAS KNAUBER AND CHAO-JUN LI* -- CHAPTER 2 Dehydrogenative Heck-type Reactions: The Fujiwara- Moritani Reaction TSUGIO KITAMURA* -- CHAPTER 3 Copper-Catalyzed Cross- Dehydrogenative-Coupling Reactions XIAOJIAN ZHENG AND ZHIPING LI* -- CHAPTER 4 Iron-Catalyzed Cross- Dehydrogenative-Coupling Reactions CHRISTOPHE DARCEL,* JEAN-BAPTISTE SORTAIS AND SAMUEL QUINTERO DUQUE -- CHAPTER 5 Cross-Dehydrogenative- Coupling Reactions Involving Allyl, Benzyl and Alkyl C-H Bonds GUO-JUN DENG,* FUHONG XIAO AND LUO YANG* -- CHAPTER 6 Aryl-Aryl Coupling -- CHAPTER 7 Asymmetric Cross- Dehydrogenative-Coupling Reactions YOSHITAKA HAMASHIMAa AND MIKIKO SODEOKA* -- CHAPTER 8 Cross-Dehydrogenative- Coupling Reactions without Metals HIDETO ITO, KIRIKA UEDA AND KENICHIRO ITAMI* -- CHAPTER 9 Cross-Dehydrogenative- Coupling Reactions with Molecular Oxygen as the Terminal Oxidant O. BASLE´ -- CHAPTER 10 Light-Assisted Cross- Dehydrogenative-Coupling Reactions LAURA FURST AND COREY R. J. STEPHENSON* -- CHAPTER 11 Mechanisms of Cross- Dehydrogenative-Coupling Reactions ALTHEA S.-K. TSANG, SOO J. PARK AND MATTHEW H. TODD* -- Subject Index.

Note: Cover -- Title Page -- Copyright -- Contents -- Preface -- Chapter 1 Introduction to Silver Chemistry -- 1.1 History and Features of Silver -- 1.1.1 Chemistry of Silver -- 1.1.2 Silver Nanoparticles -- 1.1.3 Silver Applications -- 1.2 Silver Catalysis -- 1.2.1 Alkynophilicity/Carbophilic Nature of Silver -- 1.2.2 Oxo‐ and Azaphilic Character of Silver -- 1.2.3 Halogenophilicity of Silver -- 1.2.4 Redox Chemistry of Silver -- 1.2.4.1 One‐electron Ag(I)/Ag(II) Redox Cycles -- 1.2.4.2 Two‐electron Ag(I)/Ag(III) Redox Cycle -- 1.3 Representative Examples of Silver Catalysis in the Organic Transformations -- 1.3.1 Protodecarboxylation of Carboxylic Acids -- 1.3.2 A3 Coupling Reaction -- 1.3.3 Incorporation of CO2 -- 1.3.4 Enantioselective Nitroso‐aldol Reaction -- 1.3.5 Chemoselective Cyclopropanation Using Donor-Acceptor Diazo Compounds -- 1.3.6 Homocoupling of Alkyl Grignard Reagents -- 1.3.7 Oxidative Arene Cross‐coupling -- 1.3.8 Hydroazidation of Alkynes -- 1.3.9 Isocyanide-alkyne Cycloaddition -- 1.3.10 Nitrogenation of Terminal Alkynes -- 1.3.11 Decarboxylative Alkynylation -- 1.3.12 Nitrene Transfer Reactions -- 1.3.13 Fluorination Reactions -- 1.4 Summary -- References -- Chapter 2 Silver‐catalyzed Cycloaddition Reactions -- 2.1 Introduction -- 2.2 [3+2] Cycloadditions -- 2.2.1 Cycloaddition of Azomethine Ylides -- 2.2.2 Cycloaddition of 2‐Isocyanoacetates -- 2.2.3 Cycloaddition of Azides -- 2.3 [2+2] Cycloadditions -- 2.4 [3+3] Cycloadditions -- 2.5 [4+2] Cycloadditions -- 2.5.1 Diels-Alder Reactions -- 2.5.2 Oxa‐ and Aza‐Diels-Alder Reactions -- 2.5.3 Hexadehydro Diels-Alder Reactions -- 2.6 [2+2+1] Cycloadditions -- 2.7 Miscellaneous Reactions -- 2.7.1 [2+1] Cycloaddition -- 2.7.2 [4+1] Cycloaddition -- 2.7.3 [4+2] Cycloaddition -- 2.8 Conclusion -- References -- Chapter 3 Silver‐Catalyzed Cyclizations -- 3.1 Introduction. , 3.2 Cyclization by the Formation of C-C Bonds (Cycloisomerization Reactions) -- 3.2.1 Conia‐ene Reaction -- 3.2.2 Cycloisomerization -- 3.2.2.1 Cycloisomerization of Enynes -- 3.2.2.2 Cycloisomerization of 1,n‐Allenynes -- 3.2.2.3 Cycloisomerization of 1,n‐Diyne Compounds -- 3.2.2.4 Cycloisomerization Reactions of Propargyl Compounds -- 3.2.3 Electrocyclic Reactions -- 3.2.4 Miscellaneous Reactions -- 3.3 Formation of C-N Bonds -- 3.3.1 Intramolecular Hydroamination -- 3.3.1.1 Alkynes -- 3.3.1.2 Allenes -- 3.3.1.3 Alkenes -- 3.3.2 Cycloisomerization Reactions of Alkynes -- 3.3.2.1 Imines as Nucleophiles -- 3.3.2.2 Oximes -- 3.3.2.3 Hydrazones -- 3.3.2.4 Aromatic N‐Heterocycles -- 3.3.2.5 Other Nucleophiles -- 3.4 Formation of C-O Bonds -- 3.4.1 Hydroalkoxylation -- 3.4.1.1 Alkynes -- 3.4.1.2 Allenes -- 3.4.1.3 Alkenes -- 3.4.2 Hydrocarboxylation -- 3.4.2.1 Alkynes -- 3.4.2.2 Allenes -- 3.4.2.3 Alkenes -- 3.4.3 Cycloisomerization of C-O -- 3.4.3.1 Alkynes as Partners -- 3.4.3.2 Allenes as Partners -- 3.4.4 Miscellaneous Reactions -- References -- Chapter 4 Silver‐Mediated Radical Reactions -- 4.1 Introduction -- 4.2 Protodecarboxylation -- 4.3 Radical Coupling -- 4.3.1 Formation of C-C Bonds -- 4.3.2 Formation of C-O/S/Se Bonds -- 4.3.3 Formation of C-N/P Bonds -- 4.3.4 Formation of C-Halogen Bonds -- 4.4 Radical Addition -- 4.4.1 Formation of C-C Bonds -- 4.4.2 Formation of C-Heteroatom Bonds -- 4.5 Cascade Radical Cyclizations -- 4.5.1 Formation of C-C Bonds -- 4.5.2 Formation of C-O/S/Se Bonds -- 4.5.3 Formation of C-N/P Bonds -- 4.6 Rearrangement/Migration/C-C Bond Cleavage -- 4.6.1 Aryl Migration -- 4.6.2 Radical C-C Bond Cleavage of Cycloalkanols -- 4.7 Conclusion and Perspective -- Acknowledgment -- References -- Chapter 5 Silver‐Mediated Fluorination, Perfluoroalkylation, and Trifluoromethylthiolation Reactions -- 5.1 Introduction. , 5.2 Silver‐Mediated Fluorinations -- 5.2.1 Nucleophilic Silver‐Catalyzed Fluorination -- 5.2.2 Electrophilic Silver‐Catalyzed Fluorination -- 5.2.3 Radical Silver‐Catalyzed Fluorination -- 5.2.3.1 Fluorination via Addition to Alkenes -- 5.2.3.2 Decarboxylative Fluorination -- 5.2.3.3 C-C Bond Activation -- 5.2.3.4 C-H Bond Activation -- 5.3 Silver‐Mediated Trifluoromethylations and Perfluoroalkylations -- 5.3.1 Syntheses and Properties of Perfluoroorgano Silver Compounds -- 5.3.2 Silver‐Mediated Perfluoroalkylations -- 5.3.2.1 Perfluoroorgano Silver Compounds in Copper‐Mediated Perfluoroalkylations -- 5.3.2.2 Perfluoroorgano Silver Compounds as Precursors for Radicals -- 5.3.2.3 Perfluoroorgano Silver Compounds as Nucleophilic Reagents -- 5.3.3 Silver‐Catalyzed Perfluoroalkylations -- 5.4 Silver‐Mediated and Silver‐Catalyzed Trifluoromethylthiolations -- 5.5 Conclusion and Outlook -- References -- Chapter 6 Coupling Reactions and C-H Functionalization -- 6.1 Introduction -- 6.2 Formation of Carbon-Carbon Bonds -- 6.2.1 Glaser Coupling -- 6.2.2 A3 Coupling -- 6.2.3 Oxidative Cross‐coupling and Oxidative‐Induced C-H Functionalization -- 6.2.3.1 Oxidative‐Induced C-H Functionalization -- 6.2.3.2 Oxidative Cross‐coupling -- 6.2.4 Oxidative Coupling/Cyclization Reactions -- 6.2.5 Synthesis of Biaryls -- 6.2.6 Miscellaneous Reactions -- 6.2.6.1 Isocyanide‐Involved Reactions -- 6.2.6.2 Diazo‐compound‐Involved Reactions -- 6.2.6.3 Synthesis of Perfluoroalkylated Compounds -- 6.2.6.4 C-H Carboxylation -- 6.2.6.5 Arylation and Alkylation Reactions -- 6.3 Formation of C-Heteroatom Bonds -- 6.3.1 Formation of C-Halogen Bonds -- 6.3.1.1 C-F Bond Formation -- 6.3.1.2 C-Cl Bond Formation -- 6.3.1.3 C-Br Bond Formation -- 6.3.2 Formation of C-N/P Bonds -- 6.3.2.1 C-N Bond Formation -- 6.3.2.2 C-P Bond Formation -- 6.3.3 Formation of C-O/S Bonds. , 6.3.3.1 C-O Bond Formation -- 6.3.3.2 C-S Bond Formation -- 6.3.4 Formation of C-B Bonds -- 6.3.5 Miscellaneous Reactions -- 6.4 Conclusion -- References -- Chapter 7 Silver‐Catalyzed CO2 Incorporation -- 7.1 Introduction -- 7.2 Carboxylation of Terminal Alkynes -- 7.3 Carboxylation of Aryl Boronic Esters -- 7.4 Functionalization of Terminal Epoxides -- 7.5 Cascade Carboxylation and Cyclization -- 7.5.1 Silver‐Catalyzed Sequential Carboxylation and Cyclization of Propargyl Alcohols -- 7.5.1.1 Synthesis of Cyclic Carbonate -- 7.5.1.2 Catalytic Asymmetric Synthesis of Cyclic Carbonate -- 7.5.1.3 Three‐Component Reaction of Propargyl Alcohols, Carbon Dioxide, and Nucleophiles -- 7.5.1.4 CO2‐Mediated Transformation of Propargyl Alcohols -- 7.5.1.5 Transformation of Amine Derivatives -- 7.5.1.6 Cascade Carboxylation and Cyclization of Unsaturated Amine Derivatives -- 7.5.1.7 Benzoxazine‐2‐one from o‐Alkynylaniline and Carbon Dioxide -- 7.5.1.8 Allenylamine -- 7.5.1.9 Domino Carboxylation-Cyclization-Migration of Unsaturated Amines -- 7.5.1.10 Carboxylation Involving C-C Bond Formation: Sequential Cyclization -- 7.5.1.11 Carboxylation of Enolate: Sequential Cyclization -- 7.5.1.12 Carbon Dioxide Incorporation Reaction Using Other Carbanions -- 7.6 Conclusion -- References -- Chapter 8 Silver‐Catalyzed Carbene, Nitrene, and Silylene Transfer Reactions -- 8.1 Introduction to Silver‐Mediated Carbene Transfer Reactions -- 8.2 Introduction to Cyclopropanation -- 8.2.1 General Catalysts for Cyclopropanation -- 8.2.2 Recent Advances in Silver‐Catalyzed Cyclopropanation -- 8.2.3 Recent Advances in Silver‐Catalyzed Cyclopropenation -- 8.3 Introduction to C-H Insertion -- 8.3.1 General Mechanism of C-H Functionalization via Transition Metal‐catalyzed Carbene Transfer -- 8.3.2 General Catalysts for C-H Functionalization via Carbene Transfer. , 8.3.3 Recent Advances in Silver‐Catalyzed Alkane C-H Functionalization via Carbene Transfer -- 8.3.4 Advances in Silver‐Catalyzed Carbene Insertion into Alkene or Aromatic C(sp2)-H Bonds -- 8.4 Silver‐Catalyzed Carbene Insertion into N-H Bonds -- 8.5 Silver‐Catalyzed Carbene Insertion into O-H Bonds -- 8.6 Silver‐Catalyzed Functionalization of Esters -- 8.7 Silver‐Catalyzed Si-H Functionalization -- 8.8 Summary -- 8.9 Introduction to Transition Metal‐Catalyzed Nitrene Transfer -- 8.9.1 General Catalysts for Silver‐Catalyzed Nitrene Transfer -- 8.9.2 Typical Nitrogen Sources for Silver‐Catalyzed Nitrene Transfer -- 8.9.3 General Mechanistic Features of Metal‐Catalyzed Nitrene Transfer -- 8.10 Aziridination -- 8.10.1 Intramolecular Aziridination -- 8.10.2 Intermolecular Aziridination -- 8.10.3 Mechanistic Insights into Silver‐Catalyzed Aziridination -- 8.11 C-H Bond Amidation -- 8.11.1 Intramolecular C-H Bond Amidations -- 8.11.2 Intermolecular C-H Bond Amidation -- 8.11.3 Mechanistic Aspects of Site‐selective C-H Bond Amidation -- 8.12 Silver‐Catalyzed N-N Bond Formation -- 8.13 Summary -- 8.14 Introduction to Transition Metal‐Catalyzed Silylene Transfer -- 8.15 Silver‐Mediated Silylene Transfer Reactions -- 8.15.1 Olefins -- 8.15.2 Carbonyl Compounds -- 8.15.3 C-O Bonds -- 8.15.4 Allenes -- 8.15.5 Allylic Silanes -- 8.15.6 Allylic Sulfides -- 8.16 Summary -- References -- Chapter 9 Asymmetric Silver‐Catalyzed Reactions -- 9.1 Introduction -- 9.2 Silver‐Catalyzed Mannich Reactions -- 9.2.1 Vinylogous Mukaiyama-Mannich Reactions -- 9.2.1.1 With Hoveyda-Snapper Catalysts -- 9.2.1.2 With Other Catalysts -- 9.2.2 Other Mannich‐Type Reactions -- 9.3 Silver‐Catalyzed 1,3‐Dipolar Cycloadditions -- 9.3.1 Formal 1,3‐Dipolar Cycloadditions of Glycine Imino Esters and α,β‐Unsaturated Carbonyl Compounds. , 9.3.2 Formal 1,3‐Dipolar Cycloadditions of Glycine Imino Esters and Nitroalkenes.

Note: Description based on publisher supplied metadata and other sources

Note: Description based on publisher supplied metadata and other sources

Note: Description based on publisher supplied metadata and other sources

Note: Zugl.: Hamburg, Univ., FB Geowiss., Diss, 2012 , Systemvoraussetzungen: Acrobat reader.