Palladium in Heterocyclic Chemistry - 2nd Edition - ISBN: 9780080451176, 9780080914411

Palladium in Heterocyclic Chemistry

2nd Edition

A Guide for the Synthetic Chemist

Editors: Jie Jack Li Gordon Gribble
Paperback ISBN: 9780080451176
eBook ISBN: 9780080914411
Imprint: Elsevier Science
Published Date: 30th October 2006
Page Count: 658
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Description

  • 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 halobenzothiophenes
    • 5.2 Oxidative and reductive coupling reactions
    • 5.3 Cross-coupling with organometallic reagents
    • 5.4 Sonogashira reaction
    • 5.5 Heck and intramolecular Heck reactions
    • 5.6 Carbonylation reactions
    • 5.7 Buchwald–Hartwig aminations
    • 5.8 Miscellaneous
  • Chapter 6: Furans and benzo[b]furans
    • 6.1 Synthesis of halofurans and halobenzo[b]furans
    • 6.2 Oxidative coupling/cyclization
    • 6.3 Coupling reactions with organometallic reagents
    • 6.4 Sonogashira reaction
    • 6.5 Heck, intramolecular Heck, and heteroaryl Heck reactions
    • 6.6 Heteroannulation
    • 6.7 Carbonylation and C—N and C—O bond formation
  • Chapter 7: Thiazoles and benzothiazoles
    • 7.1 Synthesis of halothiazoles
    • 7.2 Coupling reactions with organometallic reagents
    • 7.3 Sonogashira reaction
    • 7.4 Heck and heteroaryl Heck reactions
    • 7.5 Carbonylation
    • 7.6 C–N bond formation
    • 7.7 Site selective coupling reactions
  • Chapter 8: Oxazoles and benzoxazoles
    • 8.1 Introduction
    • 8.2 Synthesis of halooxazoles and halobenzoxazoles
    • 8.3 Coupling reactions with organometallic reagents
    • 8.4 Heck and heteroaryl Heck reactions
    • 8.5 Carbonylation
    • 8.6 Palladium-catalyzed amination
    • 8.7 Carbopalladation of nitriles
    • 8.8 Quaterfuran and Quinquifuran
    • 8.9 Summary
  • Chapter 9: Imidazoles
    • 9.1 Synthesis of haloimidazoles
    • 9.2 Homocoupling reaction
    • 9.3 Coupling reactions with organometallic reagents
    • 9.4 Sonogashira reaction
    • 9.5 Heck and heteroaryl Heck reactions
    • 9.6 Tsuji-Trost reaction
    • 9.7 Phosphonylation
  • Chapter 10: Pyrazines and quinoxalines
    • 10.1 Pyrazines
    • 10.2 Coupling reactions with organometallic reagents
    • 10.3 Palladium-catalyzed amination
    • 10.4 Heck reaction
    • 10.5 Carbonylation reactions
    • 10.6 Cyanation of pyrazines
    • 10.7 Deoxygenation of heteroamine-N-oxide
    • 10.8 Quinoxalines
  • Chapter 11: Pyrimidines
    • 11.1 Synthesis of pyrimidinyl halides and triflates
    • 11.2 Coupling reactions with organometallic reagents
    • 11.3 Sonogashira reaction
    • 11.4 Heck reaction
    • 11.5 The carbonylation reaction
    • 11.6 Heteroannulation
  • Chapter 12: Quinolines
    • 12.1 Synthesis of quinoline electrophiles
    • 12.2 Synthesis of quinoline nucleophiles
    • 12.3 Cross-coupling reactions with organometallic reagents
    • 12.4 Sonogashira reaction
    • 12.5 Heck reaction
    • 12.6 Miscellaneous reactions mediated by palladium
  • Chapter 13: Pyridazines
    • 13.1 Synthesis of (pseudo)halopyridazines and (pseudo)halopyridazin-3(2H)-ones
    • 13.2 Coupling reactions with organometallic reagents
    • 13.3 Sonogashira reaction
    • 13.4 Heck and intramolecular Heck reactions
    • 13.5 Carbonylation reactions
    • 13.6 C–N bond formation
  • Chapter 14: Industrial scale palladium chemistry
    • 14.1 Introduction
    • 14.2 Pharmaceutical products
    • 14.3 Cosmaceuticals
    • 14.4 Agrochemical products
    • 14.5 Material sciences
    • 14.6 Polymer chemistry
    • 14.7 New catalyst developments in fine chemical synthesis
    • 14.8 Amination
    • 14.9 Carbonylation
    • 14.10 Amidocarbonylation
  • Index

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 halobenzothiophenes
    • 5.2 Oxidative and reductive coupling reactions
    • 5.3 Cross-coupling with organometallic reagents
    • 5.4 Sonogashira reaction
    • 5.5 Heck and intramolecular Heck reactions
    • 5.6 Carbonylation reactions
    • 5.7 Buchwald–Hartwig aminations
    • 5.8 Miscellaneous
  • Chapter 6: Furans and benzo[b]furans
    • 6.1 Synthesis of halofurans and halobenzo[b]furans
    • 6.2 Oxidative coupling/cyclization
    • 6.3 Coupling reactions with organometallic reagents
    • 6.4 Sonogashira reaction
    • 6.5 Heck, intramolecular Heck, and heteroaryl Heck reactions
    • 6.6 Heteroannulation
    • 6.7 Carbonylation and C—N and C—O bond formation
  • Chapter 7: Thiazoles and benzothiazoles
    • 7.1 Synthesis of halothiazoles
    • 7.2 Coupling reactions with organometallic reagents
    • 7.3 Sonogashira reaction
    • 7.4 Heck and heteroaryl Heck reactions
    • 7.5 Carbonylation
    • 7.6 C–N bond formation
    • 7.7 Site selective coupling reactions
  • Chapter 8: Oxazoles and benzoxazoles
    • 8.1 Introduction
    • 8.2 Synthesis of halooxazoles and halobenzoxazoles
    • 8.3 Coupling reactions with organometallic reagents
    • 8.4 Heck and heteroaryl Heck reactions
    • 8.5 Carbonylation
    • 8.6 Palladium-catalyzed amination
    • 8.7 Carbopalladation of nitriles
    • 8.8 Quaterfuran and Quinquifuran
    • 8.9 Summary
  • Chapter 9: Imidazoles
    • 9.1 Synthesis of haloimidazoles
    • 9.2 Homocoupling reaction
    • 9.3 Coupling reactions with organometallic reagents
    • 9.4 Sonogashira reaction
    • 9.5 Heck and heteroaryl Heck reactions
    • 9.6 Tsuji-Trost reaction
    • 9.7 Phosphonylation
  • Chapter 10: Pyrazines and quinoxalines
    • 10.1 Pyrazines
    • 10.2 Coupling reactions with organometallic reagents
    • 10.3 Palladium-catalyzed amination
    • 10.4 Heck reaction
    • 10.5 Carbonylation reactions
    • 10.6 Cyanation of pyrazines
    • 10.7 Deoxygenation of heteroamine-N-oxide
    • 10.8 Quinoxalines
  • Chapter 11: Pyrimidines
    • 11.1 Synthesis of pyrimidinyl halides and triflates
    • 11.2 Coupling reactions with organometallic reagents
    • 11.3 Sonogashira reaction
    • 11.4 Heck reaction
    • 11.5 The carbonylation reaction
    • 11.6 Heteroannulation
  • Chapter 12: Quinolines
    • 12.1 Synthesis of quinoline electrophiles
    • 12.2 Synthesis of quinoline nucleophiles
    • 12.3 Cross-coupling reactions with organometallic reagents
    • 12.4 Sonogashira reaction
    • 12.5 Heck reaction
    • 12.6 Miscellaneous reactions mediated by palladium
  • Chapter 13: Pyridazines
    • 13.1 Synthesis of (pseudo)halopyridazines and (pseudo)halopyridazin-3(2H)-ones
    • 13.2 Coupling reactions with organometallic reagents
    • 13.3 Sonogashira reaction
    • 13.4 Heck and intramolecular Heck reactions
    • 13.5 Carbonylation reactions
    • 13.6 C–N bond formation
  • Chapter 14: Industrial scale palladium chemistry
    • 14.1 Introduction
    • 14.2 Pharmaceutical products
    • 14.3 Cosmaceuticals
    • 14.4 Agrochemical products
    • 14.5 Material sciences
    • 14.6 Polymer chemistry
    • 14.7 New catalyst developments in fine chemical synthesis
    • 14.8 Amination
    • 14.9 Carbonylation
    • 14.10 Amidocarbonylation
  • Index

Details

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

About the Editor

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