Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials 2 Volume Set

The past two decades have witnessed phenomenal advances in the synthetic, biological, and medicinal applications of organoboronate derivatives. In particular, a large number of novel synthetic processes have significantly expanded the breadth of usefulness of boronic acid derivatives as a class of substrates. As a result, most chemists in academia and industry now make use of boronic acids in synthetic chemistry, be it for Suzuki–Miyaura cross–coupling or other reactions. This in turn has created a new market for suppliers of functionalized boronic acids.
Following the huge success of the first edition, which has become THE reference source for everyone working in the field, this completely updated edition is expanded by almost 50%.
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.
From the contents:
∗ Suzuki–Miyaura cross–coupling
∗ TM–catalyzed conjugate additions
∗ Borylation of halides
∗ Direct borylations
∗ Boronic acids in materials
∗ Biological and medicinal applications
∗ Boronic acids as catalysts
∗ Trifluoroborate salts
∗ Addition to imines/Petasis reaction
∗ Catalytic allylborations
∗ Boronic acids in TM–catalyzed cascade reactions
∗ Copper catalyzed coupling to heteroatomes
∗ TM–catalyzed additions to alkenes and alkynes
Throughout, the experimental procedures described make for extremely useful reading.


Spis treści:
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 Re actions 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

Nota biograficzna:
Dennis Hall obtained his Ph.D. in 1995 from Université de Sherbrooke under the direction of Prof. Pierre Deslongchamps. Following this he 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 at the University of Alberta where he is currently Professor of Chemistry. The unifying theme of his research program is the development of new synthetic and biological applications of organoboronic acid derivatives, with topics including stereocontrolled allylation methodology, catalysis, multicomponent reactions, combinatorial chemistry and oligosaccharide recognition. Hall is on the Editorial Advisory Board of the Journal of Combinatorial Chemistry, and served as editor of a major book project (Boronic Acids: Preparation, Applications in Organic Synthesis and Medicine, Wiley–VCH, 2005). He has co–authored over 60 research publications as an independent scientist. His recent awards include the AstraZeneca Award in Chemistry (2003), the University of Alberta′s Martha Cook Piper Research Prize (2004), a Humboldt Research Fellowship (2006), a JSPS Visiting Fellowship (2007), a 2008 NSERC E.W.R. Steacie Memorial Fellowship, and the Canadian Society for Chemistry Merck–Frosst Lecture Award (2008).

Okładka tylna:
The past two decades have witnessed phenomenal advances in the synthetic, biological, and medicinal applications of organoboronate derivatives. In particular, a large number of novel synthetic processes have significantly expanded the breadth of usefulness of boronic acid derivatives as a class of substrates. As a result, most chemists in academia and industry now make use of boronic acids in synthetic chemistry, be it for Suzuki–Miyaura cross–coupling or other reactions. This in turn has created a new market for suppliers of functionalized boronic acids.
Following the huge success of the first edition, which has become THE reference source for everyone working in the field, this completely updated edition is expanded by almost 50%.
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.
From the contents:
∗ Suzuki–Miyaura cross–coupling
∗ TM–catalyzed conjugate additions
∗ Borylation of halides
∗ Direct borylations
∗ Boronic acids in materials
∗ Biological and medicinal applications
∗ Boronic acids as catalysts
∗ Trifluoroborate salts
∗ Addition to imines/Petasis reaction
∗ Catalytic allylborations
∗ Boronic acids in TM–catalyzed cascade reactions
∗ Copper catalyzed coupling to heteroatomes
∗ TM–catalyzed additions to alkenes and alkynes
Throughout, the experimental procedures described make for extremely useful reading.