Metal-catalyzed cross-coupling reactions and more / / edited by Armin de Meijere, Stefan Bräse, and Martin Oestreich |
Pubbl/distr/stampa | Weinheim an der Bergstrasse, Germany : , : Wiley-VCH, , 2014 |
Descrizione fisica | 1 online resource (3 volumes) |
Disciplina | 547.2 |
Altri autori (Persone) |
MeijereA. de
BräseStefan OestreichMartin |
Soggetto topico |
Organic compounds - Synthesis
Metal catalysts |
ISBN |
3-527-65560-3
3-527-65558-1 3-527-65561-1 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | eng |
Nota di contenuto |
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 |
Record Nr. | UNINA-9910138988103321 |
Weinheim an der Bergstrasse, Germany : , : Wiley-VCH, , 2014 | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
|
Metal-catalyzed cross-coupling reactions and more / / edited by Armin de Meijere, Stefan Bräse, and Martin Oestreich |
Pubbl/distr/stampa | Weinheim an der Bergstrasse, Germany : , : Wiley-VCH, , 2014 |
Descrizione fisica | 1 online resource (3 volumes) |
Disciplina | 547.2 |
Altri autori (Persone) |
MeijereA. de
BräseStefan OestreichMartin |
Soggetto topico |
Organic compounds - Synthesis
Metal catalysts |
ISBN |
3-527-65560-3
3-527-65558-1 3-527-65561-1 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | eng |
Nota di contenuto |
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 |
Record Nr. | UNINA-9910820712303321 |
Weinheim an der Bergstrasse, Germany : , : Wiley-VCH, , 2014 | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
|
Organic azides [[electronic resource] ] : syntheses and applications / / editors, Stefan Bräse, Klaus Banert |
Pubbl/distr/stampa | Chichester, West Sussex, U.K., : Wiley, 2010 |
Descrizione fisica | 1 online resource (537 p.) |
Disciplina |
547.04
547/.04 |
Altri autori (Persone) |
BräseStefan
BanertKlaus |
Soggetto topico |
Azides
Chemistry, Organic |
ISBN |
1-283-85876-2
0-470-68252-3 0-470-68251-5 |
Classificazione | VK 7400 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | eng |
Nota di contenuto |
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 Measurements1.4.5 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-Bonds2.3.3 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 Aziridines3.2.3 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 Acids3.4.4 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 |
Record Nr. | UNINA-9910139431303321 |
Chichester, West Sussex, U.K., : Wiley, 2010 | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
|
Organic azides [[electronic resource] ] : syntheses and applications / / editors, Stefan Bräse, Klaus Banert |
Pubbl/distr/stampa | Chichester, West Sussex, U.K., : Wiley, 2010 |
Descrizione fisica | 1 online resource (537 p.) |
Disciplina |
547.04
547/.04 |
Altri autori (Persone) |
BräseStefan
BanertKlaus |
Soggetto topico |
Azides - lemac
Chemistry, Organic |
ISBN |
1-283-85876-2
0-470-68252-3 0-470-68251-5 |
Classificazione | VK 7400 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | eng |
Nota di contenuto |
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 Measurements1.4.5 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-Bonds2.3.3 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 Aziridines3.2.3 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 Acids3.4.4 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 |
Record Nr. | UNINA-9910642778103321 |
Chichester, West Sussex, U.K., : Wiley, 2010 | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
|
Organic azides [[electronic resource] ] : syntheses and applications / / editors, Stefan Bräse, Klaus Banert |
Pubbl/distr/stampa | Chichester, West Sussex, U.K., : Wiley, 2010 |
Descrizione fisica | 1 online resource (537 p.) |
Disciplina |
547.04
547/.04 |
Altri autori (Persone) |
BräseStefan
BanertKlaus |
Soggetto topico |
Azides - lemac
Chemistry, Organic |
ISBN |
1-283-85876-2
0-470-68252-3 0-470-68251-5 |
Classificazione | VK 7400 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | eng |
Nota di contenuto |
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 Measurements1.4.5 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-Bonds2.3.3 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 Aziridines3.2.3 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 Acids3.4.4 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 |
Record Nr. | UNINA-9910830625303321 |
Chichester, West Sussex, U.K., : Wiley, 2010 | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
|