Description
This book offers a comprehensive overview of different catalytic reactions applied to the activation of chemical bonds. Each of the seven chapters covers key C-X classes where carbon is combined with another element: chlorine, fluorine, nitrogen, sulfur, oxygen, hydrogen, and carbon.
The first part of the book discusses homogeneous catalysis in the activation and transformation of C-Cl and C-F, highlighting their basic activation modes, cross-coupling, and intensive mechanisms.
The second part of the book focuses on C-N, C-S, and C-O bonds, mentioning their catalytic pathways. Finally, C-H and C-C bonds, their activation, chemical transformations, and applicability are covered. Overall, the book presents methodologies that can be applied to the efficient synthesis of drug molecules and fine chemicals. Through their presentation, the authors show that synthetic chemistry can be done in greener ways that limit hazards and pollution.
Chapter
1.2.6 Grignard Reagents as Reductant
1.2.7 Hydrazine as Reductant
1.3 Formation of C-C Bonds
1.3.6 Sonogashira Reaction
1.3.7 Decarboxylative Cross-Coupling
1.3.9 C-H Functionalization with Organic Chlorides
1.4 Formation of C-N Bonds
1.4.2 Palladium Catalysts
1.4.4 Iron and Cobalt Catalysts
1.5 Formation of C-O Bonds
1.5.2 Palladium Catalysts
1.6 Formation of C-S Bonds
1.6.2 Palladium Catalysts
1.7 Formation of C-B Bonds
1.7.1 Palladium Catalysts
1.8 Conclusion and Outlook
Chapter 2 Homogeneous Transition-Metal-Catalyzed C-F Activation
2.2 Transition-Metal-Mediated Cross-Coupling Reactions by C-F Bond Activation
2.2.1 Nickel-Mediated C-F Bond Activation
2.2.2 Palladium-Mediated C-F Bond Activation
2.2.3 Platinum-Mediated C-F Bond Activation
2.2.4 Cobalt- and Rhodium-Mediated C-F Bond Activation
2.2.5 Other-Metals-Mediated C-F Bond Activation
2.3 Transition-Metal-Catalyzed Substitution by C-F Bond Activation
2.4 Transition-Metal-Promoted Dehydrofluorination by C-F Bond Activation
2.5 The Applications of C-F Activation in Organic Synthesis
Chapter 3 Homogeneous Transition-Metal Catalyzed C-N Activation
3.2 Palladium-Catalyzed C-N Activation
3.3 Ruthenium-Catalyzed C-N Activation
3.4 Nickel-Catalyzed C-N Activation
3.5 Copper-Catalyzed C-N Activation
3.6 Iron-Catalyzed C-N Activation
3.7 Other-Transition-Metal-Catalyzed C-N Activation
3.8 Computationally and Experimentally Mechanistic Studies
Chapter 4 Catalytic Carbon-Sulfur Bond Activation and Transformations
4.2 C-S Bond Activation by Transition Metal Compounds
4.3 Catalytic C-S Cleavage in Thioesters
4.4 Catalytic C-S Cleavage in Dithioacetals
4.5 Diverse Catalytic C-S Cleavage
Chapter 5 Homogeneous Transition-Metal-Catalyzed C-O Bond Activation
5.2 Palladium-Catalyzed C-O Bond Activation
5.2.1 Kumada-Tamao-Corriu Coupling
5.2.2 Negishi Coupling (Including Zinc, Aluminum, and Manganese Reagents)
5.2.4 Suzuki-Miyaura Coupling
5.2.7 Sonogashira Reaction
5.2.8 Cross-Coupling with Other C-H Bonds and Carboxylic Acids
5.2.9 Carbonylation Reaction
5.2.10 Buchwald-Hartwig Amination
5.2.11 Other C-X Bond Formation Reactions
5.3 Nickel-Catalyzed C-O Bond Activation
5.3.1 Kumada-Tamao-Corriu Reaction
5.3.2 Negishi Coupling (Including Zinc, Aluminum, Manganese, Copper, and Indium Reagents)
5.3.3 Suzuki-Miyaura Coupling
5.3.5 Buchwald-Hartwig Amination
5.4 Other-Transition-Metal-Catalyzed C-O Bond Activation
5.4.1 Fe-Catalyzed C-O Bond Activation
5.4.2 Co-Catalyzed C-O Bond Activation
5.4.3 Cu-Catalyzed C-O Bond Activation
5.4.4 Rh-Catalyzed C-O Bond Activation
5.4.5 Ru-Catalyzed C-O Bond Activation
Chapter 6 Homogeneous Transition-Metal-Catalyzed C-H Bond Functionalization
6.2 Mechanism of C-H Cleavage
6.2.2 Electrophilic Substitution
6.2.3 Sigma Bond Metathesis
6.2.5 Metalloradical Activation
6.3 Directed C-H Oxidation
6.3.1 Directed C-H Oxygenation
6.3.2 Directed C-H Amination
6.3.3 Directed C-H Halogenation
6.3.4 Allylic C-H Oxidation
6.4.1 Directed Hydroarylation of Alkene
6.4.2 Mechanism of Alkene Hydroarylation
6.4.3 Undirected Hydroarylation of Alkene
6.4.4 Undirected Hydroarylation of Alkyne
6.4.5 Directed Hydroarylation of Alkyne
6.4.6 Oxidative Olefination
6.4.7 Annulation of C-H Bond with Alkene and Alkyne
6.5.1 Direct Arylation with Organometallic Reagents
6.5.2 Oxidative Homocoupling and Cross-Coupling of Arenes
6.5.3 Direct Arylation with Aryl Halides and Pseudohalides
6.6.1 Carbonylation to Form Aldehyde
6.6.2 Carbonylation to Form Ketone
6.6.3 Oxidative Carbonylation
6.7.1 Intramolecular Hydroacylation of Alkene
6.7.2 Intermolecular Hydroacylation of Alkene
6.7.3 Intramolecular Hydroacylation of Alkyne
6.7.4 Intermolecular Hydroacylation of Alkyne
6.8 Alkane Dehydrogenation
6.8.1 Alkane Dehydrogenation to Form Alkene
6.8.2 Dehydroaromatization
6.9 Borylation and Silylation
6.9.1 Borylation of Alkyl C-H Bond
6.9.2 Borylation of Aryl C-H Bond
6.9.3 Mechanism of Borylation
Chapter 7 Catalysis in C-C Activation
7.1 Introduction: Importance and Challenges in C-C Activation
7.2 C-C Activation of Strained Molecules
7.2.1 C-C Activation of Cyclopropane Substrates
7.2.2 C-C Activation of Cyclobutane Substrates
7.3 C-C Activation of Unstrained Molecules
7.3.1 C-C Activation of C-CN Bonds
7.3.2 C-C Activation of C-C=X Bonds (X = O, N)
7.3.3 C-C Activation of C-C-OH Bonds in Tertiary Alcohol Substrates
7.3.4 C-C Activation of C-C-OH Bonds in Secondary and Primary Alcohol Substrates
7.3.5 C-C Activation of C-Allyl Bonds
7.3.6 C-C Activation of Pincer-Type Substrates
7.3.7 C-C Activation of Miscellaneous Substrates
7.4 Summary and Perspective
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Homogeneous Catalysis for Unreactive Bond Activation
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