C-C Bond Activation

Abstract

The series Topics in Current Chemistry presents critical reviews of the present and future trends in modern chemical research. The scope of coverage is all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the non-specialist reader, whether in academia or industry, a comprehensive insight into an area where new research is emerging which is of interest to a larger scientific audience. Each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developments of the last 5 to 10 years are presented using selected examples to illustrate the principles discussed. The coverage is not intended to be an exhaustive summary of the field or include large quantities of data, but should rather be conceptual, concentrating on the methodological thinking that will allow the non-specialist reader to understand the information presented. Contributions also offer an outlook on potential future developments in the field. Review articles for the individual volumes are invited by the volume editors. Readership: research chemists at universities or in industry, graduate students. Intro; Preface; Contents; Mechanistic Studies of Transition Metal-Mediated C-C Bond Activation; 1 Introduction; 2 C-C Cleavage of Biphenylene; 3 C-C Cleavage of C-CN Bonds; 4 C-C Cleavage of C-CC Bonds; 5 C-C Cleavage of Aryl-CH3 Bonds; 6 Conclusion; References; Catalytic C-CN Bond Activation; 1 Introduction; 2 Coupling Reactions via C-CN Bond Activation; 2.1 Hydrodecyanation Reactions; 2.2 Cross-Coupling Reactions; 2.3 Silylation and Borylation Reactions; 2.4 Cycloaddition Reactions; 3 Cyanation Reactions via C-CN Bond Activation; 3.1 Cyanation of Aryl Halides and Arenes 3.2 Carbocyanation of Unsaturated Bonds4 Summary, Conclusions, Outlook; References; Metal-Organic Cooperative Catalysis in C-C Bond Activation; 1 Introduction; 1.1 Strategies for C-C Bond Cleavage; 1.2 Metal-Organic Cooperative Strategy for C-H Bond Cleavage; 2 Main Text; 2.1 Metal-Organic Cooperative C-C Single Bond Cleavage; 2.2 Metal-Organic Cooperative C-C Double Bond Cleavage; 2.3 Metal-Organic Cooperative C-C Triple Bond Cleavage; 3 Summary, Conclusions, Outlook; References; Carbon-Carbon Bond Activation with 8-Acylquinolines; 1 Introduction 2 Stoichiometric Carbon-Carbon Bond Activation Reactions2.1 Directed Cleavage of sp2-sp Carbon-Carbon Bonds; 2.2 Directed Cleavage of sp2-sp3 Carbon-Carbon Bonds; 2.2.1 Substrates Without beta-Hydrogens; 2.2.2 Substrates with beta-Hydrogens; 3 Catalytic Carbon-Carbon Bond Activation: Fragmentations; 3.1 Sp2-sp3 Carbon-Carbon Bonds: Hydroacylation; 3.2 Sp2-sp2 Carbon-Carbon Bonds: Hydroacylation; 3.3 Cross-Coupling Reactions; 4 Catalytic C-C Bond Activation Reactions: Carboacylation; 4.1 Intermolecular Carboacylation; 4.2 Intramolecular Carboacylation; 4.3 Mechanistic Considerations 4.3.1 Investigations with RhCl(PPh3)34.3.2 Investigations with [RhCl(C2H4)2]2; 5 Conclusion; References; Catalysis of Diazoalkane-Carbonyl Homologation. How New Developments in Hydrazone Oxidation Enable the Carbon Insertion Strate ... ; 1 Introduction; 2 History of Diazoalkane Ring Expansion and Chain Extension Reactions; 2.1 Protic Solvent-Promoted Reactions; 2.2 Lewis Acid-Promoted Reactions; 2.3 Lewis Acid-Catalyzed Reactions; 3 Modern Methods in Non-stabilized Diazoalkane Synthesis; 3.1 Base-Mediated Hydrolysis of N-Nitrosylamides, -Carbamates, and -Ureas; 3.2 Diazotization of Alkylamines 3.3 Bamford-Stevens Reaction and the Rise of In Situ Methodologies3.3.1 Reactions that Consume Aryldiazomethanes Without Isolation; 3.3.2 Examples in Total Synthesis; 3.4 Dehydrogenation of Hydrazones and Diazoalkane Stock Solutions; 3.4.1 Lead(IV) Oxidation of Hydrazones; 3.4.2 Azidotris(diethylamino)phosphonium Bromide with Lithium Hydrazinides; 3.4.3 Oxidation by Peracids and Catalytic Iodine; 3.4.4 Oxidation of N-(tert-Butyldimethylsilyl)hydrazones with Hypervalent Iodine; 3.4.5 Oxidation of Hydrazones by ``Activated ́́DMSO; 3.4.6 Hybrid Protocols and Modern Titration Methods