Z704660

Boronic Acids: Preparation and Application in Organic Synthesis and Medicine

applications in organic synthesis

• ISBN-10: 3-52730991-8
• ISBN-13: 978-3-52730991-7
• UNSPSC Code: 55101509

Properties

• publication info: D. Hall, John Wiley & Sons, 2005, 572 pp., hard cover

Description

General description

Dennis Hall covers all aspects of this important substance class. Starting with an introduction to the structure, properties, and preparation of boronic acid derivatives, together with an overview of their reactions and applications, the book goes on to look at metal-catalyzed borylation of alkanes and arenas, coupling reactions and rhodium-catalyzed additions of boronic acids to alkenes and carbonyl compounds.

There follows chapters on copper-promoted C-O and C-N cross-coupling of boronic acids, applications in organic synthesis, as well as alpha-haloalkylboronic esters in asymmetric synthesis. Later sections deal with cycloadditions, organoboronic acids, oxazaborolidines as asymmetric inducers, and boronic acid based receptors and sensors. With experimental procedures, this book is invaluable reading for organic, catalytic and medicinal chemists, and those working in organometallics.

Table of Contents

1. Structure, Properties, and Preparation Of Boronic Acid Derivatives. Overview of Their Reactions and Applications
2. Metal-catalyzed Borylation of Alkanes and Arenes via C–H Activation for Synthesis of Boronic Esters
3. Coupling Reactions of Areneboronic Acids or Esters with Aromatic Electrophiles
4. Rhodium-catalyzed Additions of Boronic Acids to Alkenes and Carbonyl Compounds 4.1 Introduction. 4.2 Addition of Organoboronic Acids to á,â-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.
5. Recent Advances in Copper-promoted C–Heteroatom Bond Cross-coupling Reactions with Boronic Acids and Derivatives 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.
6. Recent Advances in the Preparation of Allylboronates and Their Use in Tandem Reactions with Carbonyl Compounds
7. Nucleophilic Addition Reactions of Aryl and Alkenylboronic Acids and Their Derivatives to Imines and Iminium Ions 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.
8. (á-Haloalkyl) boronic Esters in Asymmetric Synthesis 8.1 Introduction. 8.2 General Description of (á-Haloalkyl)boronic Ester Chemistry. 8.3 Boronic Ester Intermediates in Synthesis. 8.4 Other Aspects of (á-Chloroalkyl)boronic Ester Chemistry.
9. Cycloadditions and Other Additions to Alkenyl-, Alkynyl- and Dienyl Boronic Esters
10. Organoboronic Acids and Organoborinic Acids as Brønsted–Lewis Acid Catalysts in Organic Synthesis
11. Oxazaborolidines as Asymmetric Inducers for the Reduction of Ketones and Ketimines 1
12. Boronic Acid-based Receptors and Sensors for Saccharides 1
13. Biological and Medicinal Applications of Boronic Acids 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.