18. Synthetic Applications of Organic Germanium, Tin and Lead Compounds (Excluding R3MH)

  1. Zvi Rappoport
  1. Eric Fouquet

Published Online: 5 FEB 2003

DOI: 10.1002/0470857188.ch18

The Chemistry of Organic Germanium, Tin and Lead Compounds, Volume 2

The Chemistry of Organic Germanium, Tin and Lead Compounds, Volume 2

How to Cite

Fouquet, E. (2002) Synthetic Applications of Organic Germanium, Tin and Lead Compounds (Excluding R3MH), in The Chemistry of Organic Germanium, Tin and Lead Compounds, Volume 2 (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470857188.ch18

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Laboratoire de Chimie Organique et Organométallique, Université Bordeaux I, 351, Cours de la Liberation, 33405 Talence Cedex, France. Fax: (+33) (0)5 56 84 69 94

Publication History

  1. Published Online: 5 FEB 2003
  2. Published Print: 26 NOV 2002

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Zvi Rappoport

Series Editor Information

  1. The Hebrew University, Jerusalem, Israel

ISBN Information

Print ISBN: 9780471497387

Online ISBN: 9780470857182

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Summary

This chapter contains sections titled:

  • Abbreviations

  • Introduction

  • Nucleophilic Addition

    • Nucleophilic Addition to Carbonyl Compounds

      • Background

      • Lewis Acid Activation of the Electrophile

        • Mechanisms and Diastereoselectivities Induced by γ-substituted Allyltins

        • Diastereoselectivity Induced by Chiral Aldehydes

      • Activation of the Allyltin Reagent

        • In situ Transmetallation

        • Stereochemical Outcomes

      • Catalytic Use of Lewis acid

      • Enantioselectivity

      • Other Organotin Reagents

        • Activated Allyltins

        • Allenyl- and Propargyltins

        • Buta-2,3-dienyltins

        • Alkynyltins

        • Tin cyanide

      • Conclusion

    • Nucleophilic Addition to Imines and Related Compounds

      • Reactions with Imines

        • Introduction

        • Mechanisms and Diastereoselectivity

      • Other Imino Substrates

        • Reactions with N-heterosubstituted Imines

        • Reactions with Iminium Salts

        • Reactions with Pyridines and Pyridinium Salts

      • Catalytic Enantioselective Addition

      • Other Organotin Reagents

  • Metal-catalysed Coupling Reactions

    • The Stille Coupling Reaction

      • Historical Background

        • Introduction

        • Mechanism

      • Scope and Limitations

        • Organotins

        • Substrates

        • Catalysts

      • Synthetic Applications

        • Intermolecular Couplings

        • Intramolecular Coupling

      • New Trends in the Stille Coupling Reaction

        • Solid-phase Supported Reactions

        • Unusual Media

        • Hypervalent Organotin Reagents

        • Conclusion

    • Metal Catalysed Coupling Reactions

      • Palladium-mediated Coupling Reactions

        • Carbon–carbon Coupling Reactions

        • Carbon–heteroatom Coupling Reactions

      • Copper-mediated Coupling Reactions

      • Nickel-mediated Coupling Reactions

      • Rhodium-mediated Coupling Reactions

  • Free Radical Reactions

    • Allyltins

      • Background

      • Mechanism and Reactivity

      • Functionalized Allyltins

      • The Stereoselective Approach

    • Other Organotins

      • Propargyl- and Allenyltins

      • Vinyltins

      • Miscellaneous

    • New Trends in Allyltin Transfer

  • Transmetallation Reactions

    • Historical Background and General Features

    • Tin to Lithium Exchange

      • Alkenyltins

      • α-heterosubstituted Organotins

        • Oxygen-substituted Organotins

        • Nitrogen-substituted Organotins

        • Sulphur-substituted Organotins

      • Other Organotins

    • Other Transmetallations

      • Tin to Copper Exchange

      • Tin to Boron Exchange

  • Substitution Reactions

    • Halodestannylations

      • Introduction

      • Iododestannylation

      • Bromodestannylation

      • Fluorodestannylation

    • Tin to Oxygen Substitution

    • Tin to Sulphur Substitution

  • References