Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine

Abstract

Preface. List of Authors. List of Abbreviations. 1 Structure, Properties, and Preparation Of Boronic Acid Derivatives. Overview of Their Reactions and Applications (D. G. Hall). 1.1 Introduction. 1.2 Structure and Properties of Boronic Acid Derivatives. 1.3 Synthesis of Boronic Acids and their Esters. 1.4 Isolation and Characterization. 1.5 Overview of the Reactions of Boronic Acid Derivatives. 1.6 Overview of other Applications of Boronic Acid Derivatives. 1.7 References. 2 Metal-catalyzed Borylation of Alkanes and Arenes via C-H Activation for Synthesis of Boronic Esters (T. Ishiyama and N. Miyaura). 2.1 Introduction. 2.2 Borylation of Aromatic Halides and Trif lates. 2.3 Aliphatic C-H Borylation. 2.4 Aromatic C-H Borylation. 2.5 Benzylic C-H Borylation. 2.6 References. 3 Coupling Reactions of Areneboronic Acids or Esters with Aromatic Electrophiles (A. Suzuki). 3.1 Introduction. 3.2 Coupling Reactions of Areneboronic Acid Derivatives. 3.3 Conclusion. 3.4 References. 4 Rhodium-catalyzed Additions of Boronic Acids to Alkenes and Carbonyl Compounds (K. Yoshida and T. Hayashi). 4.1 Introduction. 4.2 Addition of Organoboronic Acids to a,a-Unsaturated Ketones. 4.3 Mechanism. 4.4 Addition of Organoboronic Acids to Other Alkenes. 4.5 Addition of Organoboronic Acids to Alkynes. 4.6 Addition of Organoboronic Acids to Aldehydes and Imines. 4.7 Addition of Organoboronic Acids to Anhydrides. 4.8 Outlook. 4.9 References. 5 Recent Advances in Copper-promoted C-Heteroatom Bond Cross-coupling Reactions with Boronic Acids and Derivatives (D. M. T. Chan and P. Y. S. Lam). 5.1 General Introduction. 5.2 Copper-mediated Boronic Acid C-O and C-N Cross-coupling - Historical Background. 5.3 C(aryl)-O Cross-coupling. 5.4 C-N Cross-coupling. 5.5 C-O vs. C-N Cross-couplings. 5.6 C-N and C-O Cross-coupling with Alkenylboronic Acids. 5.7 C-S Cross-coupling. 5.8 C-N and C-O Cross-coupling with Boronic Acid Derivatives. 5.9 Mechanistic Considerations. 5.10 Other Organometalloids. 5.11 Conclusion. 5.12 Appendix. 5.13 References. 6 Recent Advances in the Preparation of Allylboronates and Their Use in Tandem Reactions with Carbonyl Compounds (J. W. J. Kennedy and D. G. Hall). 6.1 Introduction. 6.2 Preparation of Allylboronates. 6.3 Reactions of Allylboronates. 6.4 Applications of Allylboronates in Tandem Reactions with Carbonyl Compounds. 6.5 Conclusion. 6.6 References. 7 Nucleophilic Addition Reactions of Aryl and Alkenylboronic Acids and Their Derivatives to Imines and Iminium Ions (R. A. Batey). 7.1 Introduction. 7.2 Petasis Borono-Mannich Reaction: Iminium Ions Lacking Neighboring Heteroatom Functionality. 7.3 Practicality, Scope and Reaction Mechanism. 7.4 Petasis Borono-Mannich Reaction: Iminium Ions Possessing Neighboring Heteroatom Functionality. 7.5 Polymer-supported Petasis Borono-Mannich Reactions. 7.6 Other Types of Addition Reactions. 7.7 Concluding Remarks. 7.8 References. 8 (a-Haloalkyl)boronic Esters in Asymmetric Synthesis (D. S. Matteson). 8.1 Introduction. 8.2 General Description of (a-Haloalkyl)boronic Ester Chemistry. 8.3 Boronic Ester Intermediates in Synthesis. 8.4 Other Aspects of (a-Chloroalkyl)boronic Ester Chemistry. 8.5 Conclusion. 8.6 References. 9 Cycloadditions and Other Additions to Alkenyl-, Alkynyl- and Dienyl Boronic Esters (B. Carboni and F. Carreaux). 9.1 Ionic Addition. 9.2 Radical Additions. 9.3 Cycloaddition Reactions. 9.4 Metathesis Reactions. 9.5 Miscellaneous Reactions. 9.6 Conclusions. 9.7 References. 10 Organoboronic Acids and Organoborinic Acids as Bronsted-Lewis Acid Catalysts in Organic Synthesis (K. Ishihara). 10.1 Introduction. 10.2 Diarylborinic Acids. 10.3 Arylboronic Acids. 10.4 Chiral Boronate Lewis Acids. 10.5 Conclusions. 10.6 References. 11 Oxazaborolidines as Asymmetric Inducers for the Reduction of Ketones and Ketimines (B. T. Cho). 11.1 Introduction. 11.2 Oxazaborolidines. 11.3 Oxazaborolidine-catalyzed Asymmetric Reduction of Ketones. 11.4 Asymmetric Reduction of Prochiral Ketimines. 11.5 Summary and Conclusions. 11.6 References. 12 Boronic Acid-based Receptors and Sensors for Saccharides (T. D. James). 12.1 Introduction. 12.2 Fluorescence. 12.3 Colorimetric Sensors. 12.4 Electrochemical Sensors. 12.5 Assay Systems. 12.6 Polymer and Surface Bound Sensors. 12.7 Conclusions. 12.8 References. 13 Biological and Medicinal Applications of Boronic Acids (W. Yang, X. Gao, and B. Wang). 13.1 Introduction. 13.2 Boronic Acid Compounds as Enzyme Inhibitors. 13.3 Boronic Acid Compounds as Boron Neutron Capture Therapy (BNCT) Agents. 13.4 Boronic Acid Compounds as Drug (Insulin) Delivery Devices and for In Vivo Glucose Imaging. 13.5 Cell Surface Carbohydrate Recognition by Artificial Lectins - Boronolectins. 13.6 Conclusions. 13.7 References.