Boronic Acids

Following the huge success of the first edition, which has become THE reference source for everyone working in the field, this long-awaited, completely updated edition features almost 50% new content. The world-renowned chemist Prof Dennis Hall is joined by a select group of top authors to cover all modern aspects of boronic acid derivatives in one comprehensive handbook. The experimental procedures described make for extremely useful reading. From the reviews of the first edition: "...deserves to be on the bookshelf of all synthetic chemists, whether in discovery or process chemistry."

ISBN 3527325980   Volumes 2 Hardbacks ISBN13 9783527325986 (What's this?)   Weight (grammes) 1670 Publisher Wiley-VCH Verlag GmbH   Published in Weinheim Imprint Wiley-VCH Verlag GmbH   Previous ISBN 9783527309917 Format Hardback   Height (mm) 247 Publication date 19 Oct 2011   Width (mm) 175 DEWEY 547.05671   Spine width (mm) 44 DEWEY edition DC22   Academic level Professional / Scholarly Pages 726

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

"Overall, Hall's book provides an excellent starting point from which to explore the chemistry of boronic acids, but also one which gives a perspective on likely future developments. A clear positive feedback loop emerges from the material herein, whereby the take-up of new reactions and applications leads to demands for improved methods for the preparation of boronate substrates which in turn offers wider scope for further new reactivity patterns to be exploited. Hall states at the outset that his task was to provide the first comprehensive book on the chemistry and biology of boronic acids; this he has done, but at the pace of current developments, a second edition might not be so long in arriving." Angewandte Chemie IE "For some reason, this excellent book didn't get reviewed as soon as it was published but we would like to remedy this now...In conclusion, this excellent book deserves to be on the bookshelf of all synthetic chemists, whether in discovery or process chemistry." Organic Process Research & Development Journal

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