Synthesis and Application of Organoboron Compounds / / edited by Elena Fernández, Andrew Whiting

• Record Nr.: UNINA9910768440103321
• Pubbl/distr/stampa: Cham : , : Springer International Publishing : , : Imprint : Springer, , 2015
• ISBN: 3-319-13054-4
• Edizione: [1st ed. 2015.]
• Descrizione fisica: 1 online resource (VII, 331 p. 492 illus., 14 illus. in color.)
• Collana: Topics in Organometallic Chemistry, , 1436-6002 ; ; 49
• Disciplina: 547.05671
• Soggetti: Organometallic chemistry ; Catalysis; Chemical engineering; Organometallic Chemistry; Industrial Chemistry/Chemical Engineering
• Lingua di pubblicazione: Inglese
• Formato: Materiale a stampa
• Livello bibliografico: Monografia
• Note generali: Bibliographic Level Mode of Issuance: Monograph
• Nota di contenuto: Intro -- Preface -- Contents -- Boryl Anions -- 1 Introduction: History of Boryl Anions Before 2006 -- 2 Chemistry of Boryl Anions -- 2.1 Base-Stabilized Boryl Anions -- 2.2 N-Heterocyclic Boryl Anions -- 2.3 Boryl Anion Derivatives as a Counterpart of Carboanions -- 2.4 Base-Coordinated Diborane(4) as Boryl Anion Equivalents -- 3 Chemistry of Boryl-Transition Metal Complexes Derived from Boryl Anion -- 3.1 Boryl Complexes of Late Transition Metals (Groups 11-12) -- 3.2 Boryl Complexes of Early Transition Metals (Groups 3-5) -- 4 Chemistry of Boryl-Substituted Main Group Element Compounds Derived from Boryl Anions -- 4.1 Boryl-Substituted Group 13 Element Compounds -- 4.2 Boryl-Substituted Group 14 Element Compounds -- 4.3 Boryl-Substituted Group 15 Element Compounds -- 5 Summary and Outlook -- References -- Fundamental and Applied Properties of Borocations -- 1 Introduction -- 2 Fundamentals -- 2.1 Select Synthetic Considerations -- 2.2 Electrophilicity of Borocations -- 2.3 General Reactivity Pathways of Borocations with Nucleophiles -- 3 Borocations in Dehydroboration -- 3.1 Intramolecular Electrophilic Aromatic Borylation -- 3.2 Intramolecular Electrophilic Aliphatic Borylation -- 3.3 Intermolecular Electrophilic Aromatic Borylation -- 4 Borocations in ; Elemento-Boration -- 4.1 Hydroboration -- 4.2 Other Elemento-Boration Reactions -- 5 Borocations in Catalysis -- 6 Miscellaneous Applications of Borocations -- 6.1 Materials Applications -- 6.2 Borocations as Precursors to Borylenes and Boryl Radicals -- 6.3 Structural Rearrangement of Borocations -- 7 Conclusions and Future Outlook -- References -- Asymmetric Catalytic Borylation of α,beta-Unsaturated Acceptors -- 1 Introduction -- 2 Asymmetric beta-Borylation with Transition Metal Catalysts -- 2.1 Cu-Catalyzed beta-Borylation -- 2.1.1 beta-Monosubstituted Acyclic Substrates.; 2.1.2 beta,beta-Disubstituted Acyclic Substrates: Formation of Organoboronates with a Quaternary Carbon -- 2.1.3 Cyclic Compounds -- 2.1.4 α,beta-Unsaturated C=N Compounds and N-Containing Compounds -- 2.1.5 Extended Michael Acceptors -- 2.2 Rh-Catalyzed beta-Borylation -- 2.3 Ni- and Pd-Catalyzed beta-Borylation -- 3 Asymmetric beta-Borylation with Organocatalysts -- 4 Asymmetric beta-Borylation in Water -- 5 Conclusions -- References -- Reactions of Alkynylboron Compounds -- 1 Introduction -- 2 Alkynylboronates (Esters of Alkynylboronic Acids) -- 2.1 Preparations -- 2.2 Insertion Reactions -- 2.3 Cycloaddition Reactions -- 2.4 Miscellaneous -- 3 Alkynylborates (Ate-Complexes) -- 3.1 Preparations -- 3.2 Uncatalyzed Reactions -- 3.3 Transition Metal-Catalyzed Reactions -- 3.4 Reactions Through Intermediacy of Alkynyl(Triorganyl)Borates -- 4 Conclusions -- References -- Improving Transformations Through Organotrifluoroborates -- 1 Introduction -- 2 Improvements Toward Organotrifluoroborate Synthesis -- 3 Recent Advances in C-C Bond Formation with Organotrifluoroborates -- 3.1 Cross-Coupling of Novel Organotrifluoroborates -- 3.2 Improved Incorporation of Important Scaffolds -- 3.3 C-H Functionalization with Organotrifluoroborates -- 3.4 Enantioselective C-C Bond Formation -- 3.5 Radical Reactions with Organotrifluoroborates -- 4 C-Y Bond Formation from Organotrifluoroborates -- 4.1 C-O Bond Formation -- 4.2 C-N Bond Formation -- 4.3 C-X Bond Formation -- 5 Using Organotrifluoroborates to Construct Novel Scaffolds -- 6 Conclusions and Outlook -- References -- The Catalytic Dehydrocoupling of Amine-Boranes and Phosphine-Boranes -- 1 Introduction -- 2 Transition-Metal-Catalysed Dehydrocoupling of Amine-Boranes -- 2.1 General Considerations -- 2.2 Aminoboranes: Observation and Trapping -- 2.3 Linear Diborazanes.; 2.4 Early Examples of Metal-Catalysed Dehydrocoupling -- 2.5 Heterogeneous Catalysts for the Dehydrocoupling of Amine-Boranes -- 2.6 Transition-Metal-Catalysed Dehydrocoupling of H3BNH3 Promoted by Ionic Liquids -- 2.7 Homogeneous Dehydrocoupling of Amine-Boranes -- 2.7.1 Sigma Complexes of Amine-Boranes -- 2.8 Mechanistic Studies on Homogeneous Dehydrocoupling Systems -- 2.8.1 Early Transition Metals -- 2.8.2 Mid-Transition Metals -- 2.8.3 Late Transition Metals -- 2.8.4 Dehydrocoupling of Amine-Boranes Involving Ligand Cooperativity -- 2.8.5 The Role of Solvent in Dehydrocoupling Using Late Transition Metals -- 2.9 Generic Mechanisms for Dehydrocoupling of H3BNMe2H Using Transition Metals -- 2.10 Main-Group Element-Catalysed Dehydrocoupling of Amine-Boranes -- 2.10.1 Main-Group Amidoboranes: Stoichiometric Studies -- 2.10.2 Group 2 Metal-Catalysed Dehydrocoupling of Amine-Boranes -- 2.10.3 Group 3 Metal-Catalysed Dehydrocoupling of Amine-Boranes -- 2.10.4 P-Block-Catalysed Dehydrocoupling of Amine-Boranes -- 2.10.5 Frustrated Lewis Pair Dehydrogenation of Amine-Boranes -- 3 Dehydrocoupling of Phosphine-Boranes -- 3.1 Transition-Metal-Catalysed Dehydrocoupling of Phosphine-Boranes -- 3.2 Determination of the Active Catalytic Species: Hetero- or ; Homogeneous -- 3.3 Sigma Complexes and B-Agostic Interactions of Phosphine-Boranes -- 3.4 Stabilised Phosphinoboranes -- 3.5 Group 8 Metal-Catalysed Dehydrocoupling of Phosphine-Boranes -- 3.6 Mechanistic Investigations into the Rhodium-Catalysed Dehydrocoupling of Secondary Phosphine-Boranes -- 3.7 Mechanistic Investigation into the Rhodium-Catalysed Dehydrocoupling of Primary Phosphine-Boranes -- 3.8 Lewis Acid-Catalysed Dehydrocoupling of Phosphine-Boranes -- 4 Future Prospects -- References -- At the Forefront of the Suzuki-Miyaura Reaction: Advances in Stereoselective Cross-Couplings -- 1 Introduction.; 2 Applications to the Synthesis of Enantioenriched Atropisomers -- 3 Mechanistic Considerations in the Suzuki-Miyaura Cross-Coupling of sp3 Centres -- 3.1 Challenges Associated with the Coupling of Saturated Carbon Centres -- 3.2 Stereochemistry of Various Steps in the Suzuki-Miyaura Cross-Coupling Mechanism -- 4 Stereoselective C(sp3)-C(sp2) Suzuki-Miyaura Cross-Coupling Reactions -- 4.1 Stereoselective Couplings of Alkyl Boronates with Aryl or Alkenyl Halides -- 4.2 Stereoselective Couplings of Alkyl Halides and Pseudohalides with Aryl or Alkenyl Boronates -- 5 Stereoselective C(sp3)-C(sp3) Suzuki-Miyaura Cross-Coupling Reactions -- 5.1 Stereoselective Couplings of Alkyl Boranes with Alkyl Halides -- 6 Summary and Outlook -- References -- Boronic Acid-Catalyzed Reactions of Carboxylic Acids -- 1 Introduction -- 2 B(III)-Catalyzed Reactions of α,beta-Unsaturated Carboxylic Acids -- 3 B(III)-Catalyzed Dehydrative Condensation to Carboxamides -- 4 B(III)-Catalyzed Dehydrative Condensation to Carboxylic Acid Esters -- 5 B(III)-Catalyzed Dehydrative Condensation to Carboxylic Anhydrides -- 6 Other B(III)-Catalyzed Reactions -- 7 Conclusions -- References -- Reagent-Controlled Lithiation-Borylation -- 1 Introduction -- 2 Mechanism of Lithiation-Borylation Processes -- 3 α-Chloro-Stabilized Lithium Carbenoids -- 4 α-O-Stabilized Organolithiums -- 4.1 Primary Carbamates/Benzoates -- 4.2 Secondary Benzylic Carbamates -- 4.3 Secondary Allylic/Propargylic Carbamates -- 4.4 Secondary Benzoates -- 5 α-N-Stabilized Organolithiums -- 6 Conclusions and Outlook -- References -- Recent Advances in the Synthesis and Applications of Organoborane Polymers -- 1 Introduction -- 2 Synthesis of Organoborane Polymers -- 2.1 Polymer Modification Reactions on Polyolefins -- 2.2 Direct Polymerization of Borane Monomers by Chain Growth Methods.; 2.3 Side-Chain Functionalization of Conjugated Polymers -- 2.4 Boron Incorporation into the Main Chain of Conjugated Polymers -- 3 Selected Examples of Polymers and Their Applications -- 3.1 Borane Polymers as Lewis Acids and Anion Sensors -- 3.2 Luminescent Polymers Based on Boron Chelate Complexes -- 3.2.1 Boron Quinolate-Functionalized Polymers -- 3.2.2 BODIPY-Functionalized Polymers -- 3.2.3 Boron Diketonate-Functionalized Polymers -- 3.3 Boronic and Borinic Acid-Functionalized Polymers for Biomedical Applications and as Smart Materials -- 3.4 Borate and Boronium-Functionalized Polymers as Polyelectrolytes and Polymeric Ligand -- 4 Conclusions -- References -- Index.
• Sommario/riassunto: The series Topics in Organometallic Chemistry presents critical overviews of research results in organometallic chemistry. As our understanding of organometallic structure, properties and mechanisms increases, new ways are opened for the design of organometallic compounds and reactions tailored to the needs of such diverse areas as organic synthesis, medical research, biology and materials science. Thus the scope of coverage includes a broad range of topics in pure and applied organometallic chemistry, where new breakthroughs are ; being achieved that are of significance to a larger scientific audience. The individual volumes of Topics in Organometallic Chemistry are thematic. Review articles are generally invited by the volume editors.