Organoboranes In Organic Synthesis

Organoborane Chemistry deals with the chemistry of organoboranes, with emphasis on compounds containing a carbon-boron bond. The structure and physical properties of organoboranes are discussed, along with the reactions of three-coordinate and four-coordinate organoboranes, organodiboranes, and other organopolyboranes such as organotetraboranes and organopentaborane compounds. Comprised of seven chapters, this book begins with an overview of multistep synthetic or degradative reactions involving organoboron compounds, along with the nomenclature for such compounds. The next chapter examines the structure and physical properties of organoboranes, with emphasis on boron-carbon bond lengths, electronic transitions, and molecular orbital calculations. Subsequent chapters focus on three-coordinate and four-coordinate organoboranes, together with their synthesis, reactions, and properties; hydroboration and dehydroboration of organodiboranes; and the synthesis, reactions, and physical properties of other organopolyboranes such as organotetraboranes, organopentaborane compounds, and organodecaborane compounds. The final chapter is devoted to cyclic boron-carbon systems and the applications of organoboron compounds. This monograph should be of interest to organic chemists.

This monograph has been written to demonstrate to organic chemists and graduate students the strategies for controlling stereochemistry in carbon-carbon bond formations with borane intermediates. The boranes were initially found to be useful reagents by Nobel Laureate H.C. Brown. Their precursors are commercially available and derivatization is fast, clean and simple.

The leading researcher in the uses of boranes in organic synthesis here reviews his work over the past thirty-five years, covering such areas as steric strains, the nonclassical ion problem, selective reductions, hydroboration, and the organoboranes as synthetic intermediates. But more than an exposition of enormous accomplishment, the book is a scientific autobiography that will provide chemists with historical perspective on their profession. The author's detailed narrative of his own research experiences not only adds to the understanding of the present state of the study of boranes, but will serve as a stimulus to imaginative research in the future.

The widespread use of organoboron compounds justifies the efforts devoted to their synthesis, as well as toward developing an understanding of their reactivity. The nature of the mono- or diboron species is of paramount importance in determining the reversible covalent binding properties of the boron atom with both nucleophiles and electrophiles. By wedding the rich chemical potential of organoboron compounds to the ubiquity of organic scaffolds, advanced borylation reactions have the potential to open unprecedented synthetic alternatives, and new knowledge in the field should encourage chemists to use organoboron compounds. In this volume, the main objective is to provide a collection of the most useful, practical, and reliable methods, reported mainly within the last decade, for boron activation and boron reactivity. The volume covers the main concepts of organoboron compounds and includes experimental procedures, enabling newcomers to the field the instant and reliable application of the new tools in synthesis. Rather than aiming for a comprehensive coverage, the most advanced solutions for challenging transformations are introduced. To this end, a team of pioneers and leaders in the field have been assembled who discuss both the practical and conceptual aspects of this rapidly growing field.

The series Topics in Organometallic Chemistry presents critical overviews of research results in organometallic chemistry. As our understanding of organometallic structure, properties and mechanisms increases, new ways are opened for the design of organometallic compounds and reactions tailored to the needs of such diverse areas as organic synthesis, medical research, biology and materials science. Thus the scope of coverage includes a broad range of topics in pure and applied organometallic chemistry, where new breakthroughs are being achieved that are of significance to a larger scientific audience. The individual volumes of Topics in Organometallic Chemistry are thematic. Review articles are generally invited by the volume editors.

'Organic Synthesis' describes the properties and reactions of organoboranes and organosilanes, emphasizing how they can be used to provide simple solutions to a variety of synthetic problems. Compounds of boron and silicon are widely used in organic synthesis, and their study forms a core in many chemistry courses. Helpful study questions are provided at the end of each section, and the suggested further reading provides a useful guide to more advanced work in the field.