Structure, Properties, and Preparation of Boronic Acid Derivatives. Overview of Their Reactions and Applications

Abstract

This chapter contains sections titled: Introduction Structure and Properties of Boronic Acid Derivatives General Types and Nomenclature of Boronic Acid Derivatives Boronic Acids Structure and Bonding Physical Properties and Handling Safety Considerations Acidic Character Chemical Stability Boronic Acid Derivatives Boroxines Boronic Esters Dialkoxyboranes and other Heterocyclic Boranes Diboronyl Esters Azaborolidines and other Boron Heterocycles Dihaloboranes and Monoalkylboranes Trifluoroborate Salts Synthesis of Boronic Acids and their Esters Arylboronic Acids Electrophilic Trapping of Arylmetal Intermediates with Borates Transmetallation of Aryl Silanes and Stannanes Coupling of Aryl Halides with Diboronyl Reagents Direct Boronylation by Transition Metal-catalyzed Aromatic C-H Functionalization Other Methods Diboronic Acids Heterocyclic Boronic Acids Alkenylboronic Acids Electrophilic Trapping of Alkenymetal Intermediates with Borates Transmetallation Methods Transition-metal Catalyzed Coupling between Alkenyl Halides/Triflates and Diboronyl Reagents Hydroboration of Alkynes Alkene Metathesis Other Methods Alkynylboronic Acids Alkylboronic Acids Allylic Boronic Acids Chemoselective Transformations of Compounds containing a Boronic Acid (Ester)- Substituent Oxidative Methods Reductive Methods Generation and Reactions of α-Boronyl-substituted Carbanions and Radicals Reactions of (α-Haloalkyl)boronic Esters Other Transformations Isolation and Characterization Chromatography and Recrystallization Solid Supports for Boronic Acid Immobilization and Purification Diethanolaminomethyl Polystyrene Other Solid-supported Diol Resins Soluble Diol Approaches Analytical and Spectroscopic Methods for Boronic Acid Derivatives Melting Points and Combustion Analysis Mass Spectrometry Nuclear Magnetic Resonance Spectroscopy Other Spectroscopic Methods Overview of the Reactions of Boronic Acid Derivatives Metallation and Metal-catalyzed Protodeboronation Oxidative Replacement of Boron Oxygenation Amination Halogenation Carbon–Carbon Bond forming Processes Palladium-catalyzed Cross-coupling with Carbon Halides (Suzuki Coupling) Allylation of Carbonyl Compounds Uncatalyzed Additions to Imines and Iminiums Rhodium-catalyzed Additions to Aldehydes and Alkenes Heck-type Coupling to Alkenes and Alkynes Carbon–Heteroatom Bond forming Processes Copper-catalyzed Coupling with Nucleophilic Oxygen and Nitrogen-containing - Compounds Other Reactions Overview of other Applications of Boronic Acid Derivatives Use as Reaction Promoters and Catalysts Use as Protecting Groups for Diols and Diamines Use as Supports for Derivatization and Affinity Purification of Diols, Sugars, and Glycosylated Proteins Use as Receptors and Sensors for Carbohydrates and other Small Molecules Use as Antimicrobial Agents and Enzyme Inhibitors Use in Neutron Capture Therapy for Cancer Use in Transmembrane Transport Use in Bioconjugation and Labeling of Proteins and Cell Surface References