Preparation and Applications in Organic Synthesis and Medicine – Boronic Acids

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.There follow chapters on copper-promoted C-O and C-N cross-coupling of boronic acids, recent 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. The whole is rounded off with experimental procedures, making this invaluable reading for organic, catalytic and medicinal chemists, as well as those working in organometallics.

Table of 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.

About the Author :
Dennis Hall is a Professor of Chemistry at the University of Alberta (Edmonton, Canada). He was born in 1968 in northern Quebec, Canada, and was educated at Universite Sherbrooke, obtaining his Ph.D. in 1995 under the direction of Prof. Pierre Deslongchamps. Hall 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. The unifying theme of his research program is the development of new synthetic and biological applications of organoboronic acid derivatives. Ongoing projects in his laboratory cover a wide range of topics, including stereocontrolled allylation methodology, multicomponent reactions, solid-phase organic synthesis, combinatorial chemistry and oligosaccharide recognition. His recent awards include a Petro-Canada Young Innovator Award (2003), the AstraZeneca Award in Chemistry (2003), and the University of Alberta's Martha Cook Piper Research Prize (2004). He is a Fellow of the Canadian Institute of Chemistry.

Review :
"Without a doubt, this volume will be an invaluable tool for any researcher in the field of boronic acids, while still serving as a useful primer for the novice." (Journal of the American Chemical Society, October 25, 2006)