Table of Contents

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.

About the Author

Dennis Hall is a Professor of Chemistry at the University of Alberta (Edmonton, Canada). He was born in 1968 in northern Quebec, Canada, and was educated at Universite Sherbrooke, obtaining his Ph.D. in 1995 under the direction of Prof. Pierre Deslongchamps. Hall was an NSERC Postdoctoral Fellow in the laboratory of Prof. Peter G. Schultz in the Department of Chemistry at the University of California, Berkeley, and initiated his independent career in 1997. The unifying theme of his research program is the development of new synthetic and biological applications of organoboronic acid derivatives. Ongoing projects in his laboratory cover a wide range of topics, including stereocontrolled allylation methodology, multicomponent reactions, solid-phase organic synthesis, combinatorial chemistry and oligosaccharide recognition. His recent awards include a Petro-Canada Young Innovator Award (2003), the AstraZeneca Award in Chemistry (2003), and the University of Alberta's Martha Cook Piper Research Prize (2004). He is a Fellow of the Canadian Institute of Chemistry.

Reviews

"Without a doubt, this volume will be an invaluable tool for any researcher in the field of boronic acids, while still serving as a useful primer for the novice." (Journal of the American Chemical Society, October 25, 2006)