| | Table of Contents | |
| | | |
| |
| | Preface | XV |
| | List of Authors | XIX |
| | List of Abbreviations | XXI |
| 1 | Structure, Properties, and Preparation Of Boronic Acid Derivatives. Overview of Their Reactions and Applications
D. G. Hall | 1 |
| 1.1 | Introduction | 1 |
| 1.2 | Structure and Properties of Boronic Acid Derivatives | 2 |
| 1.2.1 | General Types and Nomenclature of Boronic Acid Derivatives | 2 |
| 1.2.2 | Boronic Acids | 3 |
| 1.2.2.1 | Structure and Bonding | 3 |
| 1.2.2.2 | Physical Properties and Handling | 7 |
| 1.2.2.3 | Safety Considerations | 8 |
| 1.2.2.4 | Acidic Character | 8 |
| 1.2.2.5 | Chemical Stability | 13 |
| 1.2.3 | Boronic Acid Derivatives | 14 |
| 1.2.3.1 | Boroxines | 14 |
| 1.2.3.2 | Boronic Esters | 15 |
| 1.2.3.3 | Dialkoxyboranes and other Heterocyclic Boranes | 23 |
| 1.2.3.4 | Diboronyl Esters | 24 |
| 1.2.3.5 | Azaborolidines and other Boron Heterocycles | 24 |
| 1.2.3.6 | Dihaloboranes and Monoalkylboranes | 26 |
| 1.2.3.7 | Trifluoroborate Salts | 27 |
| 1.3 | Synthesis of Boronic Acids and their Esters | 28 |
| 1.3.1 | Arylboronic Acids | 28 |
| 1.3.1.1 | Electrophilic Trapping of Arylmetal Intermediates with Borates | 28 |
| 1.3.1.2 | Transmetallation of Aryl Silanes and Stannanes | 34 |
| 1.3.1.3 | Coupling of Aryl Halides with Diboronyl Reagents | 35 |
| 1.3.1.4 | Direct Boronylation by Transition Metal-catalyzed Aromatic C–H Functionalization | 35 |
| 1.3.1.5 | Other Methods | 36 |
| 1.3.2 | Diboronic Acids | 36 |
| 1.3.3 | Heterocyclic Boronic Acids | 37 |
| 1.3.4 | Alkenylboronic Acids | 37 |
| 1.3.4.1 | Electrophilic Trapping of Alkenymetal Intermediates with Borates | 37 |
| 1.3.4.2 | Transmetallation Methods | 37 |
| 1.3.4.3 | Transition-metal Catalyzed Coupling between Alkenyl Halides/Triflates and Diboronyl Reagents | 42 |
| 1.3.4.4 | Hydroboration of Alkynes | 43 |
| 1.3.4.5 | Alkene Metathesis | 46 |
| 1.3.4.6 | Other Methods | 46 |
| 1.3.5 | Alkynylboronic Acids | 48 |
| 1.3.6 | Alkylboronic Acids | 48 |
| 1.3.7 | Allylic Boronic Acids | 49 |
| 1.3.8 | Chemoselective Transformations of Compounds containing a Boronic Acid (Ester) Substituent | 49 |
| 1.3.8.1 | Oxidative Methods | 50 |
| 1.3.8.2 | Reductive Methods | 51 |
| 1.3.8.3 | Generation and Reactions of  -Boronyl-substituted Carbanions and Radicals | 51 |
| 1.3.8.4 | Reactions of (-Haloalkyl)boronic Esters | 54 |
| 1.3.8.5 | Other Transformations | 55 |
| 1.4 | Isolation and Characterization | 57 |
| 1.4.1 | Chromatography and Recrystallization | 57 |
| 1.4.2 | Solid Supports for Boronic Acid Immobilization and Purification | 58 |
| 1.4.2.1 | Diethanolaminomethyl Polystyrene | 59 |
| 1.4.2.2 | Other Solid-supported Diol Resins | 60 |
| 1.4.2.3 | Soluble Diol Approaches | 60 |
| 1.4.3 | Analytical and Spectroscopic Methods for Boronic Acid Derivatives | 61 |
| 1.4.3.1 | Melting Points and Combustion Analysis | 61 |
| 1.4.3.2 | Mass Spectrometry | 61 |
| 1.4.3.3 | Nuclear Magnetic Resonance Spectroscopy | 61 |
| 1.4.3.4 | Other Spectroscopic Methods | 62 |
| 1.5 | Overview of the Reactions of Boronic Acid Derivatives | 62 |
| 1.5.1 | Metallation and Metal-catalyzed Protodeboronation | 62 |
| 1.5.2 | Oxidative Replacement of Boron | 63 |
| 1.5.2.1 | Oxygenation | 63 |
| 1.5.2.2 | Amination | 65 |
| 1.5.2.3 | Halogenation | 66 |
| 1.5.3 | Carbon–Carbon Bond forming Processes | 68 |
| 1.5.3.1 | Palladium-catalyzed Cross-coupling with Carbon Halides (Suzuki Coupling) | 69 |
| 1.5.3.2 | Allylation of Carbonyl Compounds | 71 |
| 1.5.3.3 | Uncatalyzed Additions to Imines and Iminiums | 73 |
| 1.5.3.4 | Rhodium-catalyzed Additions to Aldehydes and Alkenes | 73 |
| 1.5.3.5 | Heck-type Coupling to Alkenes and Alkynes | 73 |
| 1.5.4 | Carbon–Heteroatom Bond forming Processes | 73 |
| 1.5.4.1 | Copper-catalyzed Coupling with Nucleophilic Oxygen and Nitrogen-containing Compounds | 73 |
| 1.5.5 | Other Reactions | 74 |
| 1.6 | Overview of other Applications of Boronic Acid Derivatives | 76 |
| 1.6.1 | Use as Reaction Promoters and Catalysts | 76 |
| 1.6.2 | Use as Protecting Groups for Diols and Diamines | 78 |
| 1.6.3 | Use as Supports for Derivatization and Affinity Purification of Diols, Sugars, and Glycosylated Proteins | 79 |
| 1.6.4 | Use as Receptors and Sensors for Carbohydrates and other Small Molecules | 81 |
| 1.6.5 | Use as Antimicrobial Agents and Enzyme Inhibitors | 81 |
| 1.6.6 | Use in Neutron Capture Therapy for Cancer | 82 |
| 1.6.7 | Use in Transmembrane Transport | 83 |
| 1.6.8 | Use in Bioconjugation and Labeling of Proteins and Cell Surface | 84 |
| 1.7 | References | 85 |
| 2 | Metal-catalyzed Borylation of Alkanes and Arenes via C–H Activation for Synthesis of Boronic Esters
T. Ishiyama and N. Miyaura | 101 |
| 2.1 | Introduction | 101 |
| 2.2 | Borylation of Aromatic Halides and Triflates | 102 |
| 2.2.1 | Cross-coupling Reaction of Diborons | 102 |
| 2.2.2 | Cross-coupling Reaction of Pinacolborane | 104 |
| 2.3 | Aliphatic C–H Borylation | 105 |
| 2.3.1 | Rhenium-catalyzed Photochemical Reaction | 106 |
| 2.3.2 | Rhodium-catalyzed Reaction | 107 |
| 2.4 | Aromatic C–H Borylation | 109 |
| 2.4.1 | Rhenium-catalyzed Photochemical Reaction | 109 |
| 2.4.2 | Rhodium-catalyzed Reactions | 109 |
| 2.4.3 | Iridium-catalyzed Reactions | 110 |
| 2.4.4 | Catalytic Cycle | 116 |
| 2.5 | Benzylic C–H Borylation | 118 |
| | Acknowledgments | 119 |
| 2.6 | References | 119 |
| 3 | Coupling Reactions of Areneboronic Acids or Esters with Aromatic Electrophiles
A. Suzuki | 123 |
| 3.1 | Introduction | 123 |
| 3.2 | Coupling Reactions of Areneboronic Acid Derivatives | 124 |
| 3.2.1 | With Aryl Halides. Synthesis of Biaryls | 124 |
| 3.2.1.1 | Aromatic–Aromatic Coupling | 124 |
| 3.2.1.2 | Aromatic–Heteroaromatic and Heteroaromatic–Heteroaromatic Couplings | 131 |
| 3.2.1.3 | Coupling of Sterically Hindered Arylboronic Acids or ones Possessing Electron-attracting Substituents | 141 |
| 3.2.1.4 | Modified Catalysts and Ligands | 144 |
| 3.2.1.5 | Solid-phase Synthesis (Combinatorial Methodology) | 153 |
| 3.2.2 | With Other Organic Halides, including Aryl Chlorides and Electrophiles | 156 |
| 3.2.3 | Miscellaneous | 160 |
| 3.3 | Conclusion | 166 |
| 3.4 | References | 167 |
| 4 | Rhodium-catalyzed Additions of Boronic Acids to Alkenes and Carbonyl Compounds
K. Yoshida and T. Hayashi | 171 |
| 4.1 | Introduction | 171 |
| 4.2 | Addition of Organoboronic Acids to , -Unsaturated Ketones | 171 |
| 4.3 | Mechanism | 176 |
| 4.4 | Addition of Organoboronic Acids to Other Alkenes | 181 |
| 4.5 | Addition of Organoboronic Acids to Alkynes | 192 |
| 4.6 | Addition of Organoboronic Acids to Aldehydes and Imines | 195 |
| 4.7 | Addition of Organoboronic Acids to Anhydrides | 200 |
| 4.8 | Outlook | 201 |
| 4.9 | References | 201 |
| 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 | 205 |
| 5.1 | General Introduction | 205 |
| 5.2 | Copper-mediated Boronic Acid C–O and C–N Cross-coupling – Historical Background | 206 |
| 5.3 | C(aryl)–O Cross-coupling | 207 |
| 5.3.1 | Intermolecular C–O Cross-coupling | 207 |
| 5.3.2 | Intramolecular C–O Cross-coupling | 210 |
| 5.4 | C–N Cross-coupling | 212 |
| 5.4.1 | C–N (Non-heteroarene NH) Cross-coupling | 212 |
| 5.4.1.1 | Application in Solid-phase Synthesis | 214 |
| 5.4.2 | C–N (Heteroarene) Cross-coupling | 215 |
| 5.4.2.1 | Factor Xa Inhibitors | 217 |
| 5.4.2.2 | Purines | 219 |
| 5.4.2.3 | Heteroarene–Heteroarene Cross-coupling | 220 |
| 5.5 | C–O vs. C–N Cross-couplings | 221 |
| 5.6 | C–N and C–O Cross-coupling with Alkenylboronic Acids | 222 |
| 5.7 | C–S Cross-coupling | 224 |
| 5.8 | C–N and C–O Cross-coupling with Boronic Acid Derivatives | 224 |
| 5.8.1 | Boroxines, Boronic Esters and Trifluoroborate Salts | 224 |
| 5.8.2 | Alkylboronic Acids | 227 |
| 5.9 | Mechanistic Considerations | 227 |
| 5.9.1 | Electronic Effects | 227 |
| 5.9.2 | Solvent Effects | 228 |
| 5.9.3 | Ligand or Base Effects | 229 |
| 5.9.4 | Mechanism | 230 |
| 5.9.5 | Side-products | 231 |
| 5.10 | Other Organometalloids | 233 |
| 5.11 | Conclusion | 233 |
| 5.12 | Appendix | 235 |
| 5.13 | References | 238 |
| 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 | 241 |
| 6.1 | Introduction | 241 |
| 6.2 | Preparation of Allylboronates | 243 |
| 6.2.1 | Direct Methods | 243 |
| 6.2.1.1 | Allylboronates from Allylmetal Intermediates | 243 |
| 6.2.1.2 | Allylboronates from Alkenylmetal Intermediates | 244 |
| 6.2.1.3 | Allylboronates from the Hydroboration of 1,3-Butadienes and Allenes | 246 |
| 6.2.1.4 | Allylboronates from the Transition-metal Catalyzed Diboration and Silaboration of Dienes and Allenes | 247 |
| 6.2.1.5 | Allylboronates from Palladium-catalyzed Cross-coupling Reactions with Alkenyl Fragments | 249 |
| 6.2.1.6 | Allylboronates from Palladium-catalyzed Cross-coupling Reactions with Allyl Electrophiles | 249 |
| 6.2.2 | Indirect Methods | 250 |
| 6.2.2.1 | Allylboronates from Alcoholysis of Triallylboranes | 250 |
| 6.2.2.2 | Allylboronates from Homologation of Alkenylboronates | 250 |
| 6.2.2.3 | Allylboronates from Allylic Rearrangement of Alkenylboronates | 251 |
| 6.2.2.4 | Allylboronates from Isomerization of Alkenylboronates | 252 |
| 6.2.2.5 | Allylboronates by Cycloadditions of Dienylboronates | 253 |
| 6.2.2.6 | Allylboronates by Olefin Metathesis | 254 |
| 6.3 | Reactions of Allylboronates | 256 |
| 6.3.1 | Additions to Aldehydes – Formation of Homoallylic Alcohols | 256 |
| 6.3.1.1 | Stereoselectivity and Mechanism of Non-catalyzed Additions | 256 |
| 6.3.1.2 | Lewis Acid-catalyzed Additions | 257 |
| 6.3.1.3 | Stereoselective Additions with Chiral Allylboronates | 259 |
| 6.3.2 | Additions to Ketones | 263 |
| 6.3.3 | Additions to Imine Derivatives | 264 |
| 6.4 | Applications of Allylboronates in Tandem Reactions with Carbonyl Compounds | 266 |
| 6.4.1 | Allylboration as the Terminal Process | 266 |
| 6.4.1.1 | Tandem [4+2] Cycloaddition/Allylation | 266 |
| 6.4.1.2 | Tandem Hydroformylation/Intramolecular Allylation | 267 |
| 6.4.1.3 | Tandem Alkene Cross-metathesis/Allylation | 268 |
| 6.4.1.4 | Tandem Diene Hydroboration/Allylation | 269 |
| 6.4.1.5 | Tandem Diene Diborylation (Silaboration)/Allylboration | 270 |
| 6.4.1.6 | Tandem Allylic Borylation/Intramolecular Allylation | 271 |
| 6.4.2 | Allylboration as the Initiating Process | 271 |
| 6.4.2.1 | Tandem Allylation/Allylation | 271 |
| 6.4.2.2 | Tandem Allylation/Lactonization | 272 |
| 6.4.2.3 | Tandem Allylation/Dioxene Thermolysis | 273 |
| 6.5 | Conclusion | 274 |
| 6.6 | References | 274 |
| 7 | Nucleophilic Addition Reactions of Aryl and Alkenylboronic Acids and Their Derivatives to Imines and Iminium Ions
R. A. Batey | 279 |
| 7.1 | Introduction | 279 |
| 7.2 | Petasis Borono-Mannich Reaction: Iminium Ions Lacking Neighboring Heteroatom Functionality | 281 |
| 7.2.1 | Discovery of the Reaction using Paraformaldehyde | 281 |
| 7.2.2 | Reactions of Iminium Ions Derived from Simple Aldehydes | 281 |
| 7.3 | Practicality, Scope and Reaction Mechanism | 282 |
| 7.3.1 | Synthetic Benefits of the Petasis Borono-Mannich Reaction | 282 |
| 7.3.2 | Mechanistic Observations | 283 |
| 7.3.3 | Substrate Scope and the Effect of Neighboring Heteroatoms | 284 |
| 7.4 | Petasis Borono-Mannich Reaction: Iminium Ions Possessing Neighboring Heteroatom Functionality | 285 |
| 7.4.1 | Reactions of Glyoxylic Acid-derived Iminium Ions | 285 |
| 7.4.1.1 | Diastereoselective Addition Reactions to Iminium Ions Derived from Chiral Amines and Glyoxylic Acid | 289 |
| 7.4.1.2 | Enantioselective Addition Reactions to Glyoxylic Acid-derived Iminium Ions using Chiral Boronic Esters | 289 |
| 7.4.2 | Reactions of Iminium Ions Bearing -Heteroatom Substituents | 290 |
| 7.4.2.1 | Diastereoselective Addition Reactions | 290 |
| 7.4.3 | Reactions of Iminium Ions Bearing -Heteroatom Substituents | 291 |
| 7.4.4 | Addition Reactions using Iminium Ions Derived from Hydrazines, Hydroxylamines and Sulfinamides | 293 |
| 7.5 | Polymer-supported Petasis Borono-Mannich Reactions | 294 |
| 7.6 | Other Types of Addition Reactions | 297 |
| 7.6.1 | Lewis Acid Promoted Additions: Addition Reactions to N-Acyliminium Ions | 297 |
| 7.6.2 | Lewis Acid Promoted Additions of Organotrifluoroborate Salts | 298 |
| 7.6.3 | Rhodium-catalyzed Additions of Boronic Acids to N-Sulfonylimines | 299 |
| 7.6.4 | Dialkylzinc-promoted Additions of Alkenylboronic Esters to Nitrones | 301 |
| 7.6.5 | Nickel-catalyzed Couplings of Boronic Acids with Alkynes and Imines | 301 |
| 7.7 | Concluding Remarks | 302 |
| 7.8 | References | 303 |
| 8 | (-Haloalkyl)boronic Esters in Asymmetric Synthesis
D. S. Matteson | 305 |
| 8.1 | Introduction | 305 |
| 8.2 | General Description of (-Haloalkyl)boronic Ester Chemistry | 305 |
| 8.2.1 | A Brief History of Boronic Ester Chemistry | 305 |
| 8.2.2 | C2-symmetrical Boronic Esters | 306 |
| 8.3 | Boronic Ester Intermediates in Synthesis | 311 |
| 8.3.1 | Boronic Ester Intermediates without Functional Substituents | 311 |
| 8.3.2 | Halogen-substituted Boronic Esters | 315 |
| 8.3.3 | Alkoxy-substituted Boronic Esters | 316 |
| 8.3.4 | Carbonyl Substituents | 323 |
| 8.3.5 | Nitrile Substituents | 325 |
| 8.3.6 | Amino and Amido Substituents | 328 |
| 8.3.7 | Azido Substituents | 331 |
| 8.3.8 | Other Applications of (-Haloalkyl)boronic Esters | 333 |
| 8.4 | Other Aspects of (-Chloroalkyl)boronic Ester Chemistry | 334 |
| 8.4.1 | Replacement of Boronic Ester Groups | 334 |
| 8.4.2 | Chain Extension with (Dialkoxymethyl)lithium | 336 |
| 8.4.3 | (-Iodoalkyl)boronic Esters via (Phenylthiomethyl)boronic Esters | 336 |
| 8.4.4 | Free Radicals from (-Haloalkyl)boronic Esters | 337 |
| 8.4.5 | Metal Substitutions of (-Haloalkyl)boronic Esters | 338 |
| 8.5 | Conclusion | 340 |
| 8.6 | References | 340 |
| 9 | Cycloadditions and Other Additions to Alkenyl-, Alkynyl- and Dienyl Boronic Esters
B. Carboni and F. Carreaux | 343 |
| 9.1 | Ionic Addition | 343 |
| 9.1.1 | Halogenation and Hydrohalogenation | 343 |
| 9.1.2 | Addition of Organometallics | 345 |
| 9.2 | Radical Additions | 347 |
| 9.3 | Cycloaddition Reactions | 350 |
| 9.3.1 | Cyclopropanation | 350 |
| 9.3.2 | Diels–Alder Reactions | 351 |
| 9.3.2.1 | Alkenylboronates as Dienophiles | 351 |
| 9.3.2.2 | Alkynylboronates as Dienophiles | 355 |
| 9.3.2.3 | 1,3-Dienyl-1-boronates as Dienes | 356 |
| 9.3.2.4 | 1,3-Dienyl-1-boronates as Heterodienes | 360 |
| 9.3.2.5 | 1,3-Dienyl-2-boronates as Dienes | 361 |
| 9.3.3 | 1,3-Dipolar Cycloadditions | 363 |
| 9.3.3.1 | Diazoalkanes | 363 |
| 9.3.3.2 | Nitrile Oxides | 364 |
| 9.3.3.3 | Nitrones | 365 |
| 9.3.3.4 | Azomethyne Ylides | 366 |
| 9.3.4 | Other Cycloadditions | 367 |
| 9.4 | Metathesis Reactions | 368 |
| 9.5 | Miscellaneous Reactions | 370 |
| 9.6 | Conclusions | 372 |
| 9.7 | References | 373 |
| 10 | Organoboronic Acids and Organoborinic Acids as Brønsted–Lewis Acid Catalysts in Organic Synthesis
K. Ishihara | 377 |
| 10.1 | Introduction | 377 |
| 10.2 | Diarylborinic Acids | 377 |
| 10.3 | Arylboronic Acids | 381 |
| 10.4 | Chiral Boronate Lewis Acids | 389 |
| 10.4.1 | Enantioselective Carbo Diels–Alder Reactions | 389 |
| 10.4.2 | Enantioselective Hetero-Diels–Alder Reactions | 399 |
| 10.4.3 | Enantioselective Mukaiyama Aldol Reactions | 400 |
| 10.4.4 | Enantioselective Sakurai–Hosomi Allylation Reactions | 405 |
| 10.4.5 | Enantioselective Reduction | 406 |
| 10.4.6 | Enantioselective Cyclopropanation | 407 |
| 10.5 | Conclusions | 407 |
| 10.6 | References | 408 |
| 11 | Oxazaborolidines as Asymmetric Inducers for the Reduction of Ketones and Ketimines
B. T. Cho | 411 |
| 11.1 | Introduction | 411 |
| 11.2 | Oxazaborolidines | 413 |
| 11.3 | Oxazaborolidine-catalyzed Asymmetric Reduction of Ketones | 414 |
| 11.3.1 | Mechanism of OAB-catalyzed Ketone Reduction | 415 |
| 11.3.2 | Unfunctionalized Acyclic and Aryl Alkyl Ketones | 416 |
| 11.3.3 | Diaryl Ketones | 416 |
| 11.3.4 | Heterocyclic Ketones | 417 |
| 11.3.5 | Functionalized Ketones | 418 |
| 11.3.5.1 | -Halo and -Sulfonyloxy Ketones | 418 |
| 11.3.5.2 | -Hydroxy Ketones and Diketones | 421 |
| 11.3.5.3 | -Keto Acetals and Thioketals | 422 |
| 11.3.5.4 | Keto Esters and meso-Imides | 423 |
| 11.3.5.5 | ,-Enones and Ynones | 424 |
| 11.3.5.6 | -Azido and Imino Ketones | 426 |
| 11.3.5.7 | -, - and  -Keto Phosphates | 427 |
| 11.3.5.8 | -Keto Sulfides and Sulfones | 428 |
| 11.3.6 | Atropo-enantioselective Reduction | 429 |
| 11.3.7 | Kinetic Resolution of Racemic Ketones and Biaryl Lactones | 429 |
| 11.4 | Asymmetric Reduction of Prochiral Ketimines | 430 |
| 11.4.1 | Ketoxime Derivatives | 430 |
| 11.4.2 | N-Substituted Ketimines | 433 |
| 11.5 | Summary and Conclusions | 434 |
| | Acknowledgments | 436 |
| 11.6 | References | 436 |
| 12 | Boronic Acid-based Receptors and Sensors for Saccharides
T. D. James | 441 |
| 12.1 | Introduction | 441 |
| 12.2 | Fluorescence | 445 |
| 12.2.1 | Internal Charge Transfer (ICT) | 445 |
| 12.2.2 | Photoinduced Electron Transfer (PET) | 448 |
| 12.2.3 | Other Fluorescent Sensors | 458 |
| 12.3 | Colorimetric Sensors | 461 |
| 12.4 | Electrochemical Sensors | 467 |
| 12.5 | Assay Systems | 468 |
| 12.6 | Polymer and Surface Bound Sensors | 471 |
| 12.7 | Conclusions | 474 |
| 12.8 | References | 475 |
| 13 | Biological and Medicinal Applications of Boronic Acids
W. Yang, X. Gao, and B. Wang | 481 |
| 13.1 | Introduction | 481 |
| 13.2 | Boronic Acid Compounds as Enzyme Inhibitors | 484 |
| 13.2.1 | Protease Inhibitors that Bind to One Side of the Active Site | 485 |
| 13.2.2 | Boronic acid–Nucleophile Complex Formed in the Enzyme Active Site as a way to Improve Potency and Selectivity | 488 |
| 13.2.3 | Boronic Acids used for the Binding of the Non-scissile Position | 490 |
| 13.2.4 | Boronic Esters as Enzyme Inhibitors | 493 |
| 13.2.5 | Boronic Acids as Inhibitors of Glycosidases | 493 |
| 13.2.6 | Boronic Acids as Agents Targeting the Human Immunodeficiency Virus | 494 |
| 13.2.7 | Bortezomib as a Proteasome Inhibitor for Cancer Therapy: A Successful Example | 494 |
| 13.2.8 | Others | 496 |
| 13.3 | Boronic Acid Compounds as Boron Neutron Capture Therapy (BNCT) Agents | 499 |
| 13.4 | Boronic Acid Compounds as Drug (Insulin) Delivery Devices and for In Vivo Glucose Imaging | 500 |
| 13.5 | Cell Surface Carbohydrate Recognition by Artificial Lectins – Boronolectins | 503 |
| 13.6 | Conclusions | 506 |
| | Acknowledgments | 506 |
| 13.7 | References | 507 |
