Categories: Organic Chemistry >> Organometallics >> Main Group Metals

Boronic Acids

Description

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 alkenes and carbonyl compounds.

Editorial Review

Having had my own interesting experiences from laboratory work in this area (Miyaura Reaction, Suzuki Coupling, Chan-Lam Coupling), I approached this book with some curiosity. To come right to the point, "Boronic Acids" has met my expectations in nearly all respects. Several issues must be pointed out, however.

For this discussion, the book can be divided into thematically-related sections. Thus, the articles that describe the properties and synthesis of organoboronic acids and their derivatives (e.g. esters), followed by the exploration of their synthetic potential as starting materials, do an excellent job. Their uses as Lewis acids in catalysis (culminating in the chiral oxazaborolidines) are also described, as are their applications as sensors for saccharides and as enzyme inhibitors. The range of subjects covered is enormous, and readers may find themselves skipping over some of the individual sections. The focus of the book is clearly on the synthetic potential and properties of boronic acids and their derivatives. In this light, the sections on sensors and enzyme inhibitors seem rather like extra tidbits.

Generally, the readers who will be most satisfied are those who prepare organoboronic acids and their derivatives themselves. Medicinal chemists will benefit from the thorough descriptions of the many downstream reactions of these compounds. Thus, the reason for the interest in the reactions described in the book, such as the Suzuki Coupling, Chan-Lam Coupling, Borono-Mannich Reaction, is that through the use of boronic acids makes it possible for a wide range of differently substituted molecules can be generated rapidly. Even the chapter on the topic of enzyme inhibitors makes worthwhile reading. Anyone who wishes to use boronic acids as catalysts will find useful information in the general comments on this class of compounds, the synthesis pathways to boronic acids and their derivatives, and in the wealth of examples provided.

For those who need to prepare the boronic acids themselves, this monograph contains all the information worth knowing on the properties and synthesis options, while at the same time one becomes familiar with several interesting transformations. Newer reactions that have not yet been addressed in comprehensive reviews (for example, the Chan-Lam Coupling) are described in detail; only the Suzuki Coupling is given relatively little coverage, and the reader is referred to earlier treatments. Given how impressively the synthetic utility of boronic acids and their derivatives is described in the book, readers cannot help but glean some benefit for their own creativity, even if they don’t immediately need to use all of the reaction types presented.

Contents

Structure, properties, and preparation of boronic acid derivatives. Overview of their reactions and applications.
Metal-catalyzed borylation of alkanes and arenas via C-H activation for synthesis of boronic esters.
Coupling reactions of areneboronic acids or esters with aromatic electrophiles.
Rhodium-catalyzed additions of boronic acids to alkenes and carbonyl compounds.
Copper-promoted C-O and C-N cross-coupling of boronic acids.
Preparation of allylboronates and recent applications in organic synthesis.
Nulceophilic addition reactions of aryl and akenylboronic acids and their derivatives to imines and iminium ions.
Alpha-haloalkylboronic esters in asymmetric synthesis.
Cycloadditions and other additions to alkenyl- alkynyl-, and dienylboronic esters.
Organoboronic acids and organoborinic acids as Bronsted-Lewis acid catalysts in organic synthesis.
Oxazaborolidines as asymmetric inducers for the reduction of ketones and ketimines.
Boronic acid based receptors and sensors for saccharides.
Biological and medicinal applications of boronic acids.