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

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