Boronic Acids

Wiley: Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, By Dennis Hall, Second, Completely Revised Edition, 2 Volume Set:

Table of Content:

Contents to Volume 1

Foreword V

Contents to Volume 2 XIII

Preface XV

List of Contributors XIX

1 Structure, Properties, and Preparation of Boronic Acid Derivatives: Overview of Their Reactions and Applications 1 Dennis G. Hall

1.1 Introduction and Historical Background 1

1.2 Structure and Properties of Boronic Acid Derivatives 2

1.3 Preparation of Boronic Acids and Their Esters 31

1.4 Isolation and Characterization 73

1.5 Overview of the Reactions of Boronic Acid Derivatives 78

1.6 Overview of Other Applications of Boronic Acid Derivatives 97

References 109

2 Metal-Catalyzed Borylation of C–H and C–Halogen Bonds of Alkanes, Alkenes, and Arenes for the Synthesis of Boronic Esters 135 Tatsuo Ishiyama and Norio Miyaura

2.1 Introduction 135

2.2 Borylation of Halides and Triflates via Coupling of H–B and B–B Compounds 137

2.3 Borylation via C–H Activation 148

2.4 Catalytic Cycle 159

2.5 Summary 161

References 161

3 Transition Metal-Catalyzed Element-Boryl Additions to Unsaturated Organic Compounds 171 Michinori Suginome and Toshimichi Ohmura

3.1 Introduction 171

3.2 Diboration 172

3.3 Silaboration 185

3.4 Carboboration 202

3.5 Miscellaneous Element-Boryl Additions 207

3.6 Conclusion 208

References 208

4 The Contemporary Suzuki–Miyaura Reaction 213 Cory Valente and Michael G. Organ

4.1 Introduction 213

4.2 Developments Made in the Coupling of Nontrivial Substrates 215

4.3 Asymmetric Suzuki–Miyaura Cross-Couplings 241

4.4 Iterative Suzuki–Miyaura Cross-Couplings 248

4.5 Conclusions and Future Outlook 256

References 257

5 Rhodium- and Palladium-Catalyzed Asymmetric Conjugate Additions of Organoboronic Acids 263 Guillaume Berthon-Gelloz and Tamio Hayashi

5.1 Introduction 263

5.2 Rh-Catalyzed Enantioselective Conjugate Addition of Organoboron Reagents 263

5.3 Pd-Catalyzed Enantioselective Conjugate Addition of Organoboron Reagents 299

5.4 Conclusions 306

References 307

6 Recent Advances in Chan–Lam Coupling Reaction: Copper-Promoted C–Heteroatom Bond Cross-Coupling Reactions with Boronic Acids and Derivatives 315 Jennifer X. Qiao and Patrick Y.S. Lam

6.1 General Introduction 315

6.2 C–O Cross-Coupling with Arylboronic Acids 316

6.3 C–N Cross-Coupling with Arylboronic Acids 321

6.4 Substrate Selectivity and Reactivity in Chan–Lam Cross-Coupling Reaction 335

6.5 C–N and C–O Cross-Coupling with Alkenylboronic Acids 336

6.6 C–N and C–O Cross-Coupling with Boronic Acid Derivatives 338

6.7 C–S and C–Se/C–Te Cross-Coupling 346

6.8 Mechanistic Considerations 349

6.9 Other Organometalloids 354

6.10 Conclusion 355

6.11 Note Added in Proof 355

References 357

Contents to Volume 2

7 Transition Metal-Catalyzed Desulfitative Coupling of Thioorganic Compounds with Boronic Acids 363 Ethel C. Garnier-Amblard and Lanny S. Liebeskind

7.1 General Introduction 363

7.2 Boronic Acid-Thioorganic C–S Desulfitative Cross-Couplings Using Catalytic Nickel or Palladium 364

7.3 Thioorganic C–S Desulfitative Cross-Couplings Using Only Catalytic Copper 380

7.4 Miscellaneous 387

7.5 Conclusions 388

References 388

8 Catalytic Additions of Allylic Boronates to Carbonyl and Imine Derivatives 393 Tim G. Elford and Dennis G. Hall

8.1 Introduction 393

8.2 Additions to Aldehydes 395

8.3 Additions to Ketones 412

8.4 Additions to Imine Derivatives 418

8.5 Conclusions 422

References 423

9 Recent Advances in Nucleophilic Addition Reactions of Organoboronic Acids and Their Derivatives to Unsaturated C–N Functionalities 427 Timothy R. Ramadhar and Robert A. Batey

9.1 Introduction 427

9.2 Recent Advances in the Petasis Borono-Mannich Reaction 428

9.3 Reactions of N-Acyliminium Ions with Organoboronic Acids and Their Derivatives 449

9.4 Advances in Metal-Catalyzed Additions with Organoboronic Acids and Their Derivatives 455

9.5 Conclusions 472

References 473

10 Asymmetric Homologation of Boronic Esters with Lithiated Carbamates, Epoxides, and Aziridines 479 Matthew P. Webster and Varinder K. Aggarwal

10.1 Introduction 479

10.2 Lithiated Primary Alkyl Carbamates for the Homologation of Boranes and Boronic Esters 481

10.3 Lithiated Secondary Carbamates for the Homologation of Boranes and Boronic Esters 492

10.4 Benzylic N-Linked Lithiated Carbamates for the Homologation of Trialkylboranes 496

10.5 Lithiated Epoxides for the Homologation of Boronic Esters 496

10.6 Lithiated Aziridines for the Homologation of Boronic Esters 500

10.7 Conclusions 501

References 502

11 Organotrifluoroborates: Organoboron Reagents for the Twenty-First Century 507 Gary A. Molander and Ludivine Jean-Gérard

11.1 Introduction 507

11.2 Synthetic Approaches to Organotrifluoroborates 508

11.3 Elaboration of Organotrifluoroborates via Transformations of Pendant Functional Groups 509

11.4 Transition Metal-Catalyzed Processes 526

11.5 Miscellaneous Reactions of Organotrifluoroborates 537

11.6 Carbon–Carbon Bond-Forming Reactions with Activated Electrophiles 542

11.7 Conclusions 546

References 546

12 Borate and Boronic Acid Derivatives as Catalysts in Organic Synthesis 551 Joshua N. Payette and Hisashi Yamamoto

12.1 Introduction 551

12.2 Nonchiral Boron-Based Catalysis 551

12.3 Chiral Boron-Based Catalysis 561

12.4 Conclusion 587

References 587

13 Applications of Boronic Acids in Chemical Biology and Medicinal Chemistry 591 Nanting Ni and Binghe Wang

13.1 Introduction 591

13.2 Boronic Acids as Potential Medicinal Agents 591

13.3 Probes for Detecting Reactive Oxygen Species 597

13.4 MRI and PET Agents for in vivo Carbohydrate Imaging 603

13.5 Carbohydrate Biomarker Binding Agents and Sensors 607

13.6 Conclusions 617

References 617

14 Boronic Acids in Materials Chemistry 621 Jie Liu and John J. Lavigne

14.1 Introduction 621

14.2 Linear Boronate-Linked Materials 624

14.3 Macrocycles and Cages 637

14.4 Networks 658

14.5 Summary and Outlook 671

References 673

Index 677