Note: Intro -- Metal-Catalyzed Cross-Coupling Reactions and More -- Contents to Volume 1 -- Preface -- List of Contributors -- Chapter 1 Mechanistic Aspects of Metal-Catalyzed C,C- and C,X-Bond Forming Reactions -- 1.1 Mechanisms of Cross-Coupling Reactions -- 1.1.1 The Earlier Mechanistic Proposal: The Stille Reaction -- 1.1.2 The Oxidative Addition -- 1.1.2.1 Cis-Complexes in the Oxidative Addition -- 1.1.2.2 The Role of Alkene and Anionic Ligands -- 1.1.2.3 Cross-Couplings in the Presence of Bulky Phosphines -- 1.1.2.4 N-Heterocyclic Carbenes as Ligands -- 1.1.2.5 Palladacycles as Catalysts -- 1.1.2.6 Involvement of Pd(IV) in Catalytic Cycles -- 1.1.2.7 Oxidative Addition of Stannanes to Pd(0) -- 1.1.3 The Transmetallation in the Stille Reaction -- 1.1.3.1 Isolation of the Transmetallation Step -- 1.1.3.2 Dissociative Mechanistic Proposals -- 1.1.3.3 Cyclic and Open Associative Transmetallation -- 1.1.3.4 The Copper Effect -- 1.1.3.5 Transmetallation in the Suzuki-Miyaura Reaction -- 1.1.3.6 Transmetallation in the Negishi Reaction -- 1.1.3.7 Transmetallation in the Hiyama Reaction -- 1.1.3.8 Couplings Catalyzed by Copper and Gold -- 1.1.3.9 Couplings Catalyzed by Iron and Cobalt -- 1.1.4 Reductive Elimination -- 1.2 Palladium-Catalyzed α-Arylation of Carbonyl Compounds and Nitriles -- 1.3 Formation of C-X (X = N, O, S) Bonds in Metal-Catalyzed Reactions -- 1.3.1 Reductive Elimination to Generate C-N, C-O, and C-S Bonds from Organopalladium(II) Complexes -- 1.3.2 Nickel- and Copper-Catalyzed Formation of C-X Bonds -- 1.4 Summary and Outlook -- List of Abbreviations -- References -- Chapter 2 State-of-the-Art in Metal-Catalyzed Cross-Coupling Reactions of Organoboron Compounds with Organic Electrophiles -- 2.1 Introduction -- 2.1.1 Catalytic Cycle -- 2.1.2 Improvements toward More Efficient Cross-Coupling Conditions. , 2.1.2.1 Development of New Phosphine and NHC Ligands -- 2.1.2.2 Usage of Masked Boron Derivatives as Cross-Coupling Partners -- 2.1.2.3 Lewis Acids as Additives -- 2.1.2.4 Adjusting the Nucleophilicity of Organoboron Cross-Coupling Partners -- 2.1.2.5 Copper Salts as Additives -- 2.2 Advances in Cross-Coupling Reactions for the Formation of C(sp2)-C(sp2) Bonds -- 2.2.1 Background -- 2.2.2 Recent Developments in the Use of New Electrophilic Coupling Partners -- 2.2.2.1 Chlorides -- 2.2.2.2 Fluorides -- 2.2.2.3 Pseudohalides -- 2.2.3 Recent Developments in Organoboron Cross-Coupling Partners -- 2.2.3.1 Trifluoroborate Salts -- 2.2.3.2 N-Methyliminodiacetic Acid (MIDA) Boronates -- 2.2.3.3 Other Organoboron Cross-Coupling Partners -- 2.2.4 Synthesis of Enantiomerically Enriched Atropisomers -- 2.3 Advances in the Cross-Coupling Reactions for the Formation of C(sp3)-C(sp2) or C(sp3)-C(sp3) Bonds -- 2.3.1 Background -- 2.3.1.1 Stereochemistry -- 2.3.2 Cross-Couplings between Unsaturated sp2 Carbon Centers and sp3 Carbon Centers -- 2.3.2.1 Cross-Couplings between sp3 Alkyl Halides and sp2 Alkenyl or Aryl Boron Derivatives -- 2.3.2.2 Cross-Couplings between sp3 Alkyl Boron Derivatives with sp2 Alkenyl or Aryl Halides -- 2.3.3 Cross-Couplings between sp3 Carbon Centers with sp3 Carbon Centers -- 2.3.3.1 Cross-Couplings between Achiral Substrates -- 2.3.3.2 Stereoselective Cross-Coupling Reactions of sp3 Alkyl Halides with sp3 Alkylboranes -- 2.4 Experimental Procedures -- 2.4.1 2,6-Dimethoxy-2',6'-dimethylbiphenyl (55) -- 2.4.2 4-Methoxybiphenyl (R = C(O)NEt2, R' = H, Ar = 4-methoxyphenyl) -- 2.4.3 1-Phenylnaphthalene (ROH = naphthol, Ar = Ph) -- 2.4.4 1-(3,5-Dimethoxyphenyl)-5-phenylpentan-3-one (Ralkyl-BF3K = 197, R1 = CH2CH2Ph, R' = 3,5-dimethoxybenzene) -- 2.4.5 1-Phenyl-1-(4-acetylphenyl-ethane (ArI = 4-iodoacetophenone). , 2.4.6 Naphthalene-1,8-diamido (dan) derivative (Ar = Ph) -- 2.4.7 2-Methyl-5-phenylpentyl benzyl(phenyl)carbamate (Ralkyl = Me,X = Br, R'alkyl = CH2CH2CH2Ph) -- 2.5 Summary and Outlook -- References -- Chapter 3 Pd-Catalyzed Cross-Coupling with Organometals Containing Zn, Al, Zr, and so on - The Negishi Coupling and Its Recent Advances -- 3.1 Background and Discovery -- 3.1.1 Why Metals? Why Transition Metals? -- 3.1.2 Why Transition Metal-Catalyzed Organometallic Reactions? -- 3.2 Discovery of the Pd- or Ni-Catalyzed Cross-Coupling Reactions of Organometals Containing Zn, Al, Zr, and B -- 3.3 The Current Scope of the Pd- or Ni-Catalyzed Cross-coupling and Its Application to the Synthesis of Natural Products and Other Complex Organic Compounds -- 3.3.1 Cross-Coupling between Two Unsaturated (Aryl, Alkenyl, and/or Alkynyl) Groups -- 3.3.1.1 Aryl-Aryl Coupling -- 3.3.1.2 Aryl-Alkenyl and Alkenyl-Aryl Couplings -- 3.3.1.3 Alkenyl-Alkenyl Coupling -- 3.3.1.4 Pd-Catalyzed Alkynylation -- 3.3.2 Cross-Coupling Involving One Allyl, Benzyl, or Propargyl Group -- 3.3.2.1 1,4-Dienes via Pd-Catalyzed Alkenyl-Allyl and Allyl-Alkenyl Coupling and 1,4-Enynes by Pd-Catalyzed Alkynyl-Allyl Coupling -- 3.3.2.2 Benzyl-Aryl, Aryl-Benzyl Coupling -- 3.3.2.3 Allylbenzene Derivatives via Pd-Catalyzed Alkenyl-Benzyl Coupling and Aryl-Allyl and Allyl-Aryl Coupling -- 3.3.2.4 Benzylated Alkynes via Pd-Catalyzed Alkynyl-Benzyl Coupling and Aryl-Propargyl as well as Propargyl-Aryl Coupling -- 3.3.2.5 1,4-Diynes via Alkynyl-Propargyl Coupling -- 3.3.2.6 Synthesis of Natural Products Containing 1,4-Diene and Allylated Arenes by Pd-Catalyzed Allylation, Benzylation, and Propargylation -- 3.3.3 Cross-Coupling between Two Allyl, Benzyl, and/or Propargyl Groups -- 3.3.3.1 1,5-Dienes and 1,5-Enynes via Pd-Catalyzed Cross-Couplings with Allyl, Benzyl, Propargyl Electrophiles. , 3.3.3.2 1,5-Dienes and 1,5-Enynes via Pd-Catalyzed Homoallyl-Alkenyl Coupling and Homopropargyl-Alkenyl Coupling -- 3.3.3.3 Bibenzyls, Homoallylarenes, 1,5-Dienes, Homopropargylarenes, and 1,5-Enynes via Pd-Catalyzed Negishi Coupling -- 3.3.4 Cross-Coupling Involving Alkylmetals and/or Alkyl Electrophiles Other Than Those Containing Allyl, Benzyl, and/or Propargyl Groups -- 3.3.4.1 Pd-Catalyzed Alkyl-Alkyl Coupling -- 3.3.4.2 Ni-Catalyzed Alkyl-Alkyl Coupling -- 3.3.4.3 Catalytic Asymmetric Cross-Coupling Reactions with Secondary Alkyl Halides -- 3.3.5 Pd-Catalyzed Acylation, Cyanation, and α-Substitution of Enolates and Related Derivatives -- 3.3.5.1 Pd-Catalyzed Acylation -- 3.3.5.2 Pd-Catalyzed Cyanation -- 3.3.5.3 Pd-Catalyzed α-Substitution of Enolates and Related Derivatives -- 3.4 Zr-Catalyzed Asymmetric Carboalumination of Alkenes (ZACA) ZACA-Pd- or Cu-Catalyzed Cross-Coupling Sequential Processes as a General Route to Enantiomerically Enriched Chiral Organic Compounds -- 3.4.1 Zirconium-Catalyzed Asymmetric Carboalumination of Alkenes (ZACA Reaction) -- 3.4.1.1 Historical and Mechanistic Background of Carbometallation of Alkenes and Alkynes with Alkylzirconocene Derivatives -- 3.4.1.2 Catalytic Asymmetric Carbometallation of Alkenes Proceeding via Dzhemilev Ethylmagnesiations -- 3.4.2 Current Summary of Development and Application of the ZACA Reaction and Conclusion -- 3.4.2.1 ZACA-Pd-Catalyzed Cross-Coupling Sequential Processes for the Synthesis of Deoxypolypropionates and Related Compounds -- 3.4.2.2 ZACA-Lipase-Catalyzed Acetylation-Pd- or Cu-Catalyzed Cross-Coupling Synergy to Chiral Organic Compounds -- 3.5 Representative Experimental Procedures -- 3.5.1 (2Z,4S)-5-(tert-Butyldimethylsilyloxy)-2-phenyl-4-methyl-2-pentene -- 3.5.2 (2Z,4E,6E)-Ethyl Trideca-2,4,6-trienoate -- 3.5.3 (2Z)-2-Allyl-3,7-dimethylocta-2,6-dien-1-ol. , 3.5.4 Ethyl 2-(4-Phenylbuta-1,3-diynyl)benzoate -- 3.5.4.1 (E)-1-Chloro-4-phenyl-1-buten-3-yne -- 3.5.4.2 Ethyl 2-(4-Phenylbuta-1,3-diynyl)benzoate -- 3.5.5 O-tert-Butyldiphenylsilyl-protected (3S,5E)-3,9-Dimethyl-6-isopropyl-5,8-decadien-1-ol -- 3.5.5.1 (1E)-1-Iodo-2-isopropyl-5-methyl-1,4-hexadiene -- 3.5.5.2 O-tert-Butyldiphenylsilyl-protected (3S,5E)-3,9-Dimethyl-6-isopropyl-5,8-decadien-1-ol -- 3.5.6 1,3-Diphenylpropyne -- 3.5.7 (4S)-4-Phenyl-1-pentene -- 3.5.8 (R)-2-Phenylpropan-1-ol -- Acknowledgments -- References -- Chapter 4 Carbon-Carbon Bond Forming Reactions Mediated by Organozinc Reagents -- 4.1 Introduction -- 4.2 Methods of Preparation of Zinc Organometallics -- 4.2.1 Direct Insertion of Zn(0) into Organohalides -- 4.2.2 Transmetallation Reactions -- 4.2.2.1 Transmetallation Reactions with Main-Group and Transition Metal Organometallics -- 4.2.2.2 Boron-Zinc Exchange Reactions -- 4.2.3 Direct Zincation Reactions -- 4.2.4 Halogen-Zinc Exchange Reactions -- 4.2.5 Hydro- and Carbozincation Reactions -- 4.3 Uncatalyzed Cross-Coupling Reactions of Organozinc Reagents -- 4.4 Copper-Catalyzed Cross-Coupling Reactions of Organozinc Reagents -- 4.4.1 Cross-Coupling with C(sp)- or C(sp2)-Electrophiles -- 4.4.2 Cross-Coupling Reactions with C(sp3)-Electrophiles -- 4.5 Transition-Metal-Catalyzed Cross-Coupling Reactions of Organozinc Reagents -- 4.5.1 Cross-Coupling Reactions of C(sp2)-Organozinc Reagents -- 4.5.1.1 Palladium-Catalyzed Cross-Coupling Reactions -- 4.5.1.2 Nickel-Catalyzed Cross-Coupling Reactions -- 4.5.1.3 Rhodium-Catalyzed Cross-Coupling Reactions -- 4.5.1.4 Cobalt-Catalyzed Cross-Coupling Reactions -- 4.5.1.5 Iron-Catalyzed Cross-Coupling Reactions -- 4.5.2 Cross-Coupling Reactions of Alkynylzinc Reagents -- 4.5.2.1 Cross-Coupling with C(sp2)-Electrophiles -- 4.5.2.2 Cross-Coupling with C(sp3)-Electrophiles. , 4.5.3 Cross-Coupling Reactions of C(sp3)-Organozinc Reagents.

Note: Intro -- The Chemistry of Mycotoxins -- Contents -- List of Contributors -- About the Authors -- 1: Introduction -- 2: Aflatoxins -- 2.1 Biological Properties -- 2.2 Total Syntheses of Aflatoxins -- 2.2.1 Total Syntheses of Racemic Aflatoxins -- 2.2.2 Enantioselective Total Syntheses of Aflatoxins -- 2.3 Syntheses of Aflatoxin Building Blocks -- 2.3.1 Syntheses of Building Blocks for Aflatoxins B2 and G2 -- 2.3.2 Syntheses of Building Blocks for Aflatoxins B1 and G1 -- 2.3.3 Synthesis of a Building Block for Aflatoxin M2 -- 2.3.4 Enantioselective Syntheses of Aflatoxin Building Blocks -- 2.4 Syntheses of Biosynthetic Aflatoxin Precursors -- 3: Citrinin -- 3.1 General -- 3.2 Total Syntheses of Citrinin -- 4: Ergot Alkaloids -- 4.1 Structural Subclasses of Ergot Alkaloids -- 4.1.1 Tricyclic Precursors of Ergot Alkaloids -- 4.1.2 Clavine-Type Alkaloids -- 4.1.3 Ergoamides -- 4.1.4 Ergopeptines -- 4.1.5 Related Structures -- 4.2 Biological Properties -- 4.3 Total Syntheses -- 4.3.1 Enantioselective Synthesis via Pd-Catalyzed Oxidative Kinetic Resolution: (-)-Aurantioclavine -- 4.3.2 Asymmetric Alkenylation of Sulfinyl Imines: (-)-Aurantioclavine -- 4.3.3 The IMDAF-Approach to ()-Cycloclavine -- 4.3.4 Enantioselective Pd-Catalyzed Domino Cyclization Strategy to (+)-Lysergic acid, (+)-Lysergol, and (+)-Isolysergol -- 4.3.5 Intramolecular Vinylogous Mannich Approach to Rugulovasines A and B -- 4.3.6 Intermolecular Vinylogous Mannich Approach to Setoclavine -- 4.3.7 Biomimetic Three-Step Synthesis of Clavicipitic Acids -- 5: Fumonisins -- 5.1 Biological Properties -- 5.2 Total Syntheses -- 5.2.1 Total Synthesis of Fumonisin B1 -- 5.2.2 Enantioselective Total Synthesis of Fumonisin B2 -- 5.2.3 Total Synthesis of AAL-toxin TA1 -- 6: Ochratoxins -- 6.1 Biological Properties -- 6.2 Total Syntheses. , 6.2.1 Enantioselective Total Synthesis of (R)-Ochratoxin α and Ochratoxins A, B, and C -- 6.2.2 Total Syntheses of Racemic Ochratoxins α and Ochratoxins A, B, and C -- 6.2.3 Total Syntheses of All Stereoisomers of Ochratoxin A -- 7: Patulin -- 7.1 General -- 7.2 Total Syntheses of Patulin -- 8: Trichothecenes -- 8.1 Biological Properties -- 8.2 Total Syntheses -- 8.2.1 Non-Macrocyclic Trichothecenes -- 8.2.1.1 Synthesis of Trichodermin -- 8.2.1.2 Synthesis of Anguidine -- 8.2.1.3 Synthesis of Sporol -- 8.2.2 Macrocyclic Trichothecenes -- 8.2.2.1 Synthesis of Verrucarol -- 8.2.2.2 Synthesis of Verrucarin A -- 8.2.2.3 Synthesis of Roridin E and Baccharin B5 -- 9: Resorcylic Acid Lactones -- 9.1 Biological Properties -- 9.2 Total Syntheses -- 9.2.1 Total Syntheses of Zearalenone -- 9.2.1.1 Total Synthesis of (S)-Zearalenone by Nicolaou -- 9.2.1.2 Total Synthesis of (S)-Zearalenone by Barrett -- 9.2.2 Total Synthesis of Zearalenol -- 9.2.3 Total Synthesis of Radicicol -- 9.2.4 Total Synthesis of Hypothemycin -- 9.2.5 Total Synthesis of Aigialomycin D -- 9.2.6 Total Synthesis of Pochonin C -- 10: (Thio)diketopiperazines -- 10.1 Biological Properties -- 10.2 Total Syntheses -- 10.2.1 DKP Total Syntheses -- 10.2.2 TDKP Total Syntheses -- 11: Alternaria Metabolites -- 11.1 Biological Properties -- 11.2 Total Syntheses -- 11.2.1 Total Synthesis of Alternariol and Alternariol 9-Methyl Ether -- 11.2.2 Total Synthesis of Altenuene and Isoaltenuene -- 11.2.3 Total Synthesis of Dehydroaltenusin -- 11.2.4 Total Synthesis of Neoaltenuene -- 11.2.5 Total Synthesis of Tenuazonic Acid -- 12: Skyrins -- 12.1 Biological Properties -- 12.2 Syntheses of Skyrin Model Systems -- 12.3 Total Syntheses of Skyrins -- 13: Xanthones -- 13.1 Xanthones -- 13.1.1 Bikaverin -- 13.1.2 Pinselin and Pinselic Acid -- 13.1.3 Sterigmatocystin and Derivatives. , 13.1.3.1 Isolation and Structural Determination -- 13.1.3.2 Biosynthesis -- 13.1.3.3 Bioactivity -- 13.1.3.4 Synthesis -- 13.1.4 Nidulalin A -- 13.2 Tetrahydroxanthones -- 13.2.1 Blennolides -- 13.2.2 Dihydroglobosuxanthone -- 13.2.3 Diversonol -- 13.2.4 Diversonolic Esters -- 13.3 Hexahydroxanthones -- 13.3.1 Applanatins -- 13.3.2 Isocochlioquinones -- 13.3.3 Monodictysins -- 13.4 Xanthone Dimers and Heterodimers -- 13.4.1 Acremoxanthones -- 13.4.2 Vinaxanthones -- 13.4.3 Xanthofulvin -- 13.5 Tetrahydroxanthone Dimers and Heterodimers -- 13.5.1 Parnafungins -- 13.5.2 Ascherxanthone -- 13.5.3 Secalonic Acids -- 13.5.4 Xanthoquinodins -- 13.5.5 Beticolins -- 13.5.6 Dicerandrols -- 13.5.7 Microsphaerins -- 13.5.8 Neosartorin -- 13.5.9 Phomoxanthones -- 13.5.10 Rugulotrosins -- 13.5.11 Sch 42137 -- 13.5.12 Sch 54445 -- 13.5.13 Xanthonol -- 14: Cytochalasans -- 14.1 Biological Properties -- 14.2 Total Syntheses -- 14.2.1 Total Synthesis of Cytochalasin B and L-696,474 -- 14.2.2 Total Synthesis of Proxiphomin -- 14.2.3 Total Synthesis of Cytochalasin H -- 14.2.4 Total Synthesis of Cytochalasin G -- 14.2.5 Total Synthesis of Cytochalasins D and O -- 14.2.6 Total Synthesis of (-)-Aspochalasin B -- 14.2.7 Total Synthesis of Zygosporin E -- 15: Peptidic Mycotoxins -- 15.1 Biological Properties -- 15.2 Total Syntheses -- 15.2.1 Total Synthesis of Pithomycolide -- 15.2.2 Total Synthesis of Ustiloxins D and F -- 15.2.3 Total Synthesis of Malformin C -- 15.2.4 Total Synthesis of Unguisin A -- Abbreviations -- References -- Author Index -- Subject Index.

Note: Organic Azides Syntheses and Applications -- Contents -- Foreword -- Preface -- List of Contributors -- Abbreviations -- PART 1: Synthesis and Safety -- 1: Lab-scale Synthesis of Azido Compounds: Safety Measures and Analysis -- 1.1 Introduction -- 1.2 Properties that Impose Restrictions on Lab-scale Handling of Azides -- 1.2.1 Hydrazoic Acid and Its Metal Salts -- 1.2.2 Organic Azides -- 1.3 Laboratory Safety Instructions for the Small-scale Synthesis of Azido Compounds -- 1.4 Analyzing Safety-related Properties of Azides -- 1.4.1 Impact Sensitivity Testing -- 1.4.2 Friction Sensitivity Testing -- 1.4.3 ESD Testing -- 1.4.4 Thermoanalytical Measurements -- 1.4.5 Calorimetric and Gravimetric Stability Tests -- 1.4.6 Koenen Test -- References -- 2: Large-scale Preparation and Usage of Azides -- 2.1 Introduction -- 2.2 Precursor Azides, Technical Production and Properties -- 2.2.1 Sodium azide (NaN3) -- 2.2.2 Trimethylsilyl Azide (TMSA)14 -- 2.2.3 Diphenylphosphoryl Azide (DPPA)14 -- 2.2.4 Tributyltin Azide (TBSnA) -- 2.2.5 Azidoacetic Acid Ethyl Ester (AAE)14 -- 2.2.6 Tetrabutylammonium Azide (TBAA)14 -- 2.2.7 Others -- 2.3 Examples for the Use of Azides on a Technical Scale -- 2.3.1 Addition of NaN3 to Multiple CC- or CN-Bonds -- 2.3.2 Addition of Alk-N3 and Ar-N3 to Multiple CC- and/or CN-Bonds -- 2.3.3 Carboxylic Acid Azides: Precursors for Isocyanates -- 2.3.4 Organic Azides: Ring Opening Reaction on Oxiranes and Aziridines: Paclitaxel, Tamiflu® -- 2.3.5 Organic Azides: Protective Group, Masked Amines -- 2.3.6 Organic Azides: Cross-linking Agents for Polymers -- 2.4 The Future of Commercial-scale Azide Chemistry -- References -- 3: Synthesis of Azides -- 3.1 Introduction -- 3.2 Synthesis of Alkyl Azides -- 3.2.1 Classic Nucleophilic Substitutions: Azides from Halides, Sulfonates, Sulfites, Carbonates, Thiocarbonates and Sulfonium Salts. , 3.2.2 Azides by Ring Opening of Epoxides and Aziridines -- 3.2.3 Azides by the Mitsunobu Reaction -- 3.2.4 Alkyl Azides from Amines -- 3.2.5 Alkyl Azides from Carbon Nucleophiles and Electron-poor Sulfonyl Azides -- 3.3 Synthesis of Aryl Azides -- 3.3.1 Nucleophilic Aromatic Substitution: SNAr Reactions -- 3.3.2 Aryl Azides from Diazonium Compounds -- 3.3.3 Aryl Azides from Organometallic Reagents -- 3.3.4 Aryl Azides by Diazo Transfer -- 3.3.5 Aryl Azides from Hydrazines and from Nitrosoarenes -- 3.4 Synthesis of Acyl Azides -- 3.4.1 Acyl Azides from Mixed Acid Chlorides -- 3.4.2 Acyl Azides from Mixed Anhydrides -- 3.4.3 Acyl Azides by Direct Conversion of Carboxylic Acids -- 3.4.4 Acyl azides by Direct Conversion of Aldehydes -- 3.4.5 Acyl Azides by Direct Conversion of Acylhydrazines -- 3.4.6 Acyl Azides from N-acylbenzotriazoles -- References -- 4: Azides by Olefin Hydroazidation Reactions -- 4.1 Introduction -- 4.2 Conjugate Addition of Hydrazoic Acid and Its Derivatives -- 4.3 Addition of Hydrazoic Acid and Its Derivatives to Non-Activated Olefins -- 4.4 Cobalt-Catalyzed Hydroazidation -- 4.4.1 Optimization of the Cobalt-Catalyzed Hydroazidation Reaction -- 4.4.2 Scope of the Hydroazidation of Olefins -- 4.4.3 Further Process Optimization -- 4.4.4 One-pot Functionalization of the Azide Products -- 4.4.5 Mechanistic Investigations -- 4.5 Conclusion -- References -- PART 2: Reactions -- 5: The Chemistry of Vinyl, Allenyl, and Ethynyl Azides -- 5.1 Introduction and Early Synthetic Methods for Vinyl Azides -- 5.2 Routes to Vinyl Azides Developed in the Period 1965-70 -- 5.3 New Methods to Prepare Vinyl Azides -- 5.4 Reactions of Vinyl Azides -- 5.5 The Chemistry of Allenyl Azides -- 5.6 Generation of Ethynyl Azides -- 5.7 Conclusion -- Acknowledgment -- References -- 6: Small Rings by Azide Chemistry -- 6.1 Introduction -- 6.2 2H-Azirines. , 6.3 Aziridines -- 6.3.1 Aziridines via Nitrene Intermediates -- 6.3.2 Aziridines via Triazolines -- 6.3.3 Aziridines from Epoxides or 1,2-Diols -- 6.3.4 Aziridines from Vinyl Azides via 2H-Azirines -- 6.4 Triaziridines -- 6.5 Azetidinones -- References -- 7: Schmidt Rearrangement Reactions with Alkyl Azides -- 7.1 Introduction and Early Attempts (1940-60) -- 7.2 Schmidt Reactions of Alkyl Azides with Carbonyl Compounds -- 7.2.1 Intramolecular Reactions -- 7.2.2 Intermolecular Reactions -- 7.2.3 Reactions of Hydroxyalkyl Azides -- 7.3 Schmidt Reactions of Alkyl Azides with Carbocations -- 7.4 Metal-mediated Schmidt Reactions of Alkyl Azides with Alkenes and Alkynes -- 7.5 Reactions of Alkyl Azides with α,β-Unsaturated Ketones -- 7.6 Reactions of Alkyl Azides with Epoxides -- 7.7 Combined Schmidt Rearrangement Cascade Reactions -- 7.8 Schmidt Rearrangements in the Total Synthesis of Natural Products -- 7.9 Schmidt Rearrangements of Alkyl Azides in the Synthesis of Interesting Non-natural Products -- 7.10 Schmidt Rearrangements of Hydroxyalkyl Azides toward Biologically Relevant Compounds -- 7.11 Final Comments -- Acknowledgments -- References -- 8: Radical Chemistry with Azides -- 8.1 Introduction -- 8.2 Addition of the Azidyl Radical onto Alkenes -- 8.2.1 Metal Generated Azidyl Radicals -- 8.2.2 Azidation using Hypervalent Iodine Compounds -- 8.2.3 Halogen Azides as a Source of Azidyl Radicals -- 8.2.4 Electrochemically Generated Azidyl Radicals -- 8.3 Azidation of Carbon Centered Radicals -- 8.3.1 Radical Azidation -- 8.3.2 Radical Additions to Alkyl and Aryl Azides -- 8.4 Aminyl and Amidyl Radicals via Reduction of Azides -- 8.4.1 Photo-and Electrochemical Reductions of Organic Azides to Amines -- 8.4.2 Reduction of Organic Azides with Metals -- 8.4.3 Reduction of Organic Azides with SmI2. , 8.4.4 Radical Reactions of Organic Azides with Tributyltin Hydride -- 8.4.5 Radical Reductions of Organic Azides with Silanes -- 8.4.6 Radical Reactions of Organic Azides with FeCl2 -- 8.5 Fragmentation Reaction of α-Azidoalkyl Radicals -- 8.6 Conclusions -- References -- 9: Cycloaddition Reactions with Azides: An Overview -- 9.1 Huisgen 1,3-dipolar cycloaddition -- 9.2 Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) -- 9.2.1 General Aspects of the CuAAC Reaction -- 9.2.2 Mechanism of the CuAAC Reaction -- 9.3 Acceleration of the Click Reaction -- 9.3.1 Addition of Ligands -- 9.3.2 Addition of Base -- 9.4 Copper-free Click Chemistry -- 9.5 Ruthenium-Catalyzed Azide-Alkyne Cycloaddition (RuAAC) -- 9.6 Use of Other Metals for the Cycloaddition of Azides and Alkynes: Ni(II), Pt(II), Pd(II) -- 9.7 Cycloaddition Reactions with Azides for the Synthesis of Tetrazoles -- 9.7.1 Intermolecular Approaches -- 9.7.2 Intermolecular Approaches -- 9.8 Click Chemistry for the Synthesis of Dihydrotriazoles -- 9.9 Cycloaddition Reactions with Azides to Give Thiatriazoles -- References -- 10: Dipolar Cycloaddition Reactions in Peptide Chemistry -- 10.1 Introduction -- 10.2 Amino Acid Derivatives by DCR -- 10.3 Peptide Backbone Modifications by DCR -- 10.4 Other Peptide Modifications by DCR -- 10.5 Macrocyclization by DCR -- 10.6 Dendrimers and Polymers -- 10.7 Isotopic Labeling by DCR -- 10.8 Perspective -- References -- 11: Photochemistry of Azides: The Azide/Nitrene Interface -- 11.1 Introduction -- 11.2 Photochemistry of Hydrazoic Acid (HN3) -- 11.3 Photochemistry of Alkyl Azides -- 11.4 Photochemistry of Vinyl Azides -- 11.5 Photochemistry of Carbonyl Azides and Azide Esters -- 11.5.1 Photochemistry of Azide Esters -- 11.6 Photochemistry of Phenyl Azide and Its Simple Derivatives -- 11.6.1 Photochemistry of Phenyl Azide. , 11.6.2 Photochemistry of Simple Derivatives of Phenyl Azide -- 11.6.3 Photochemistry of Polynuclear Aromatic Azides -- 11.7 Conclusion -- Acknowledgments -- References -- 12: Organoazides and Transition Metals -- 12.1 Introduction -- 12.2 Metal Complexes Co-crystallized with an Organoazide -- 12.3 Cationic Metal Complexes with Organoazide Containing Anions -- 12.4 Metal Complexes with Ligands Bearing a Non-coordinating Organoazide Unit -- 12.5 Metal Complexes with an Intact, Coordinating and Linear Organoazide Ligand -- 12.6 Metal Complexes with an Intact, Coordinating but Bent Organoazide Ligand -- 12.7 Organoazides Reacting with Other Metal Bound Ligands -- References -- PART 3: Material Sciences -- 13: Azide-containing High Energy Materials -- 13.1 Introduction -- 13.2 Organic Azides -- 13.2.1 Alkyl and Alkenyl Substituted Azides -- 13.2.2 Aryl Substituted Azides -- 13.2.3 Heterocycles Containing Azide Groups -- Acknowledgments -- References -- 14: Azide Chemistry in Rotaxane and Catenane Synthesis -- 14.1 Introduction -- 14.2 Purely Organic Rotaxanes and Catenanes -- 14.2.1 With Cucurbiturils (CB) and Cyclodextrins (CD) as Cyclic Components -- 14.2.2 Based on Hydrogen Bonding or on Organic Donor-Acceptor Complexes -- 14.3 Transition Metal Templated Approaches -- 14.3.1 Cu(I) Assembled Rotaxanes -- 14.3.2 Cu(I) as Both a Template and a Catalyst -- 14.4 Conclusion -- References -- PART 4: Application in Bioorganic Chemistry -- 15: Aza-Wittig Reaction in Natural Product Syntheses -- 15.1 Introduction -- 15.2 Intermolecular Aza-Wittig Reaction -- 15.2.1 Reaction with Carbonyl Compounds -- 15.2.2 Reaction with Heterocumulene Derivatives -- 15.3 Intramolecular Aza-Wittig Reaction -- 15.3.1 Functionalized Phosphazenes Containing an Aldehyde Group -- 15.3.2 Functionalized Phosphazenes containing a Ketone Group. , 15.3.3 Functionalized Phosphazenes Containing an Ester Group.