Boronic acids [[electronic resource] ] : preparation and applications in organic synthesis and medicine / / edited by Dennis G. Hall

• Record Nr.: UNINA9910144324903321
• Pubbl/distr/stampa: Weinheim, : Wiley-VCH; Chichester, : John Wiley, c2005
• ISBN: 1-280-52116-3; 9786610521166; 3-527-60682-3; 3-527-60654-8; 1-60119-357-2
• Descrizione fisica: 1 online resource (577 p.)
• Altri autori (Persone): HallDennis
• Disciplina: 547.05671
• Soggetti: Organic acids; Organoboron compounds; Organic acids - Therapeutic use; Organoboron compounds - Therapeutic use; Organic acids - Synthesis; Organoboron compounds - Synthesis; Electronic books.
• Lingua di pubblicazione: Inglese
• Formato: Materiale a stampa
• Livello bibliografico: Monografia
• Note generali: Description based upon print version of record.
• Nota di bibliografia: Includes bibliographical references and index.
• Nota di contenuto: Boronic Acids; Table of Contents; Preface; List of Authors; List of Abbreviations; 1 Structure, Properties, and Preparation Of Boronic Acid Derivatives. Overview of Their Reactions and Applications; 1.1 Introduction; 1.2 Structure and Properties of Boronic Acid Derivatives; 1.2.1 General Types and Nomenclature of Boronic Acid Derivatives; 1.2.2 Boronic Acids; 1.2.2.1 Structure and Bonding; 1.2.2.2 Physical Properties and Handling; 1.2.2.3 Safety Considerations; 1.2.2.4 Acidic Character; 1.2.2.5 Chemical Stability; 1.2.3 Boronic Acid Derivatives; 1.2.3.1 Boroxines; 1.2.3.2 Boronic Esters; 1.2.3.3 Dialkoxyboranes and other Heterocyclic Boranes1.2.3.4 Diboronyl Esters; 1.2.3.5 Azaborolidines and other Boron Heterocycles; ; 1.2.3.6 Dihaloboranes and Monoalkylboranes; 1.2.3.7 Trifluoroborate Salts; 1.3 Synthesis of Boronic Acids and their Esters; 1.3.1 Arylboronic Acids; 1.3.1.1 Electrophilic Trapping of Arylmetal Intermediates with Borates; 1.3.1.2 Transmetallation of Aryl Silanes and Stannanes; 1.3.1.3 Coupling of Aryl Halides with Diboronyl Reagents; 1.3.1.4 Direct Boronylation by Transition Metal-catalyzed Aromatic C-H Functionalization; 1.3.1.5 Other Methods; 1.3.2 Diboronic Acids1.3.3 Heterocyclic Boronic Acids; 1.3.4 Alkenylboronic Acids; 1.3.4.1 Electrophilic Trapping of Alkenymetal Intermediates with Borates; 1.3.4.2 Transmetallation Methods; 1.3.4.3 Transition-metal Catalyzed Coupling between Alkenyl Halides/Triflates and Diboronyl Reagents; 1.3.4.4 Hydroboration of Alkynes; 1.3.4.5 Alkene Metathesis; 1.3.4.6 Other Methods; 1.3.5 Alkynylboronic Acids; 1.3.6 Alkylboronic Acids; 1.3.7 Allylic Boronic Acids; 1.3.8 Chemoselective Transformations of Compounds containing a Boronic Acid (Ester) Substituent; 1.3.8.1 Oxidative Methods; 1.3.8.2 Reductive Methods1.3.8.3 Generation and Reactions of α-Boronyl-substituted Carbanions and Radicals; 1.3.8.4 Reactions of (α-Haloalkyl)boronic Esters; 1.3.8.5 Other Transformations; 1.4 Isolation and Characterization; 1.4.1 Chromatography and Recrystallization; 1.4.2 Solid Supports for Boronic Acid Immobilization and Purification; 1.4.2.1 Diethanolaminomethyl Polystyrene; 1.4.2.2 Other Solid-supported Diol Resins; 1.4.2.3 Soluble Diol Approaches; 1.4.3 Analytical and Spectroscopic Methods for Boronic Acid Derivatives; 1.4.3.1 Melting Points and Combustion Analysis; 1.4.3.2 Mass Spectrometry1.4.3.3 Nuclear Magnetic Resonance Spectroscopy; 1.4.3.4 Other Spectroscopic Methods; 1.5 Overview of the Reactions of Boronic Acid Derivatives; 1.5.1 Metallation and Metal-catalyzed Protodeboronation; 1.5.2 Oxidative Replacement of Boron; 1.5.2.1 Oxygenation; 1.5.2.2 Amination; 1.5.2.3 Halogenation; 1.5.3 Carbon-Carbon Bond forming Processes; 1.5.3.1 Palladium-catalyzed Cross-coupling with Carbon Halides (Suzuki Coupling); 1.5.3.2 Allylation of Carbonyl Compounds; 1.5.3.3 Uncatalyzed Additions to Imines and Iminiums; 1.5.3.4 Rhodium-catalyzed Additions to Aldehydes and Alkenes
• Sommario/riassunto: For the first time, the whole field of organoboronic acids is presented in one comprehensive handbook.Professor Dennis Hall, a rising star within the community, covers all aspects of this important substance class, including applications in chemistry, biology and medicine.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 al