Palladium in Heterocyclic Chemistry

Palladium in Heterocyclic Chemistry

A Guide for the Synthetic Chemist

2nd Edition - October 20, 2006

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  • Editors: Jie Jack Li, Gordon Gribble
  • eBook ISBN: 9780080465845

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Description

Palladium chemistry, despite its immaturity, has rapidly become an indispensable tool for synthetic organic chemists. Heterocycles are of paramount importance in the pharmaceutical industry and palladium chemistry is one of the most novel and efficient ways of making heterocycles. Today, palladium-catalyzed coupling is the method of choice for the synthesis of a wide range of biaryls and heterobiaryls. The number of applications of palladium chemistry to the syntheses of heterocycles has grown exponentially. These developments highlight the need for a monograph dedicated solely to the palladium chemistry in heterocycles and this book provides a comprehensive explanation of the subject. The principal aim of the book is to highlight important palladium-mediated reactions of heterocycles with emphasis on the unique characteristics of individual heterocycles. 1. Palladium chemistry of heterocycles has its “idiosyncrasies” stemming from their different structural properties from the corresponding carbocyclic aryl compounds. Even activated chloroheterocycles are sufficiently reactive to undergo Pd-catalyzed reactions. As a consequence of &agr and &bgr activation of heteroaryl halides, Pd-catalyzed chemistry may take place regioselectively at the activated positions, a phenomenon rarely seen in carbocyclic aryl halides. In addition, another salient peculiarity in palladium chemistry of heterocycles is the so-called "heteroaryl Heck reaction". For instance, while intermolecular palladium-catalyzed arylations of carbocyclic arenes are rare, palladium-catalyzed arylations of azoles and many other heterocycles readily take place. Therefore, the principal aim of this book is to highlight important palladium-mediated reactions of heterocycles with emphasis on the unique characteristics of individual heterocycles. 2. A myriad of heterocycles are biologically active and therefore of paramount importance to medicinal and agricultural chemists. Many heterocycle-containing natural products (they are highlighted in boxes throughout the text) have elicited great interest from both academic and industrial research groups. Recognizing the similarities between the palladium chemistry of arenes and heteroarenes, a critical survey of the accomplishments in heterocyclic chemistry will keep readers abreast of such a fast-growing field. We also hope this book will spur more interest and inspire ideas in such an extremely useful area. This book comprises a compilation of important preparations of heteroaryl halides, boranes and stannanes for each heterocycle. The large body of data regarding palladium-mediated polymerization of heterocycles in material chemistry is not focused here; neither is coordination chemistry involving palladium and heterocycles. Many heterocycle-containing natural products (highlighted throughout the text) have elicited great interest from both academic and industrial research groups. Recognizing the similarities between the palladium chemistry of arenes and heteroarenes, a critical survey of the accomplishments in heterocyclic chemistry keeps readers abreast of this fast-growing field. It is also hoped that this book will stimulate more interest and inspire new ideas in this exciting area.

Key Features

  • Contains the most up-to-date developments in this fast-moving field
  • Includes 3 new chapters
  • Incorporates material from selected well-respected authors on heterocyclic chemistry

Readership

Medicinal Chemists, Organic Chemists

Table of Contents

  • 1. Introduction
    2. Pyrroles
    3. Indoles
    4. Pyridines
    5. Thiophenes And Benzo[B]Thiophenes
    6. Furans And Benzo[B]Furans
    7. Thiazoles And Benzothiazoles
    8. Oxazoles And Benzoxazoles
    9. Imidazoles
    10. Pyrazines And Quinoxalines
    11. Pyrimidines
    12. Quinolines
    13. Pyridazines
    14. Industrial Scale Palladium Chemistry

Product details

  • No. of pages: 658
  • Language: English
  • Copyright: © Elsevier Science 2006
  • Published: October 20, 2006
  • Imprint: Elsevier Science
  • eBook ISBN: 9780080465845

About the Editors

Jie Jack Li

Affiliations and Expertise

Pfizer Global Research and Development, Ann Arbor, Michigan, USA

Gordon Gribble

Gordon Gribble is Emeritus Professor and Research Professor of Chemistry at Dartmouth College, Hanover, USA, where he has been since 1968. His research interests cover several areas of organic chemistry, most of which involve synthesis, including novel indole chemistry, triterpenoid synthesis, and new synthetic methodology. Prof Gribble also has a deep interest in naturally occurring organohalogen compounds, and in the chemistry of wine and wine making.

Affiliations and Expertise

Dartmouth Professor, Chemistry, Dartmouth College, Hanover, USA

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