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 agric

Key Features

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

Readership

Medicinal Chemists, Organic Chemists

Table of Contents

  • Copyright page
  • Contributing authors
  • Preface to the first edition
  • Preface to the second edition
  • Abbreviations
  • Chapter 1: An introduction to palladium catalysis
    • 1.1 Oxidative coupling/cyclization
    • 1.2 Cross-coupling reactions with organometallic reagents
    • 1.3 The Sonogashira reaction
    • 1.4 The Heck, intramolecular Heck, and heteroaryl Heck reactions
    • 1.5 Carbonylation reactions
    • 1.6 The Pd-catalyzed C–P bond formation
    • 1.7 Palladium-catalyzed C–N bond and C–O bond-forming reactions
    • 1.8 The Tsuji–Trost reaction
    • 1.9 The Wacker-type reactions
    • 1.10 Mori–Ban, Hegedus, and Larock indole syntheses
  • Chapter 2: Pyrroles
    • 2.1 Synthesis of pyrrolyl halides
    • 2.2 Oxidative coupling/cyclization
    • 2.3 Coupling reactions with organometallic reagents
    • 2.4 Sonogashira reaction
    • 2.5 Heck and intramolecular Heck reactions
    • 2.6 Carbonylation
    • 2.7 C-N bond formation reactions
    • 2.8 Miscellaneous
  • Chapter 3: Indoles
    • 3.1 Synthesis of indolyl halides
    • 3.2 Oxidative coupling/cyclization
    • 3.3 Coupling reactions with organometallic reagents
    • 3.4 The Sonogashira coupling
    • 3.5 Heck couplings
    • 3.6 Carbonylation
    • 3.7 C–N bond formation reactions
    • 3.8 Miscellaneous
  • Chapter 4: Pyridines
    • 4.1 Synthesis of halopyridines
    • 4.2 Coupling reactions with organometallic reagents
    • 4.3 Sonogashira reaction
    • 4.4 Heck and intramolecular Heck reactions
    • 4.5 Buchwald–Hartwig aminations(C–N bond formation)
    • 4.6 Direct C–C bond formation
    • 4.7 Summary
  • Chapter 5: Thiophenes and benzo[b]thiophenes
    • 5.1 Preparation of halothiophenes and halob

Details

No. of pages:
658
Language:
English
Copyright:
© 2006
Published:
Imprint:
Elsevier Science
Print ISBN:
9780080451176
Electronic ISBN:
9780080914411

About the authors

Jie Jack Li

Affiliations and Expertise

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

Gordon Gribble

Gordon Gribble is the Dartmouth Professor of Chemistry at Dartmouth College, Hanover, USA. His research program covers several areas of organic chemistry, most of which involve synthesis, including novel indole chemistry, triterpenoid synthesis, DNA intercalation, 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

Department of Chemistry, Dartmouth College, Hanover, NH, USA