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Related Experiment Videos

Palladium-Catalyzed Stille Couplings with Fluorous Tin Reactants.

Masahide Hoshino1, Peter Degenkolb, Dennis P. Curran

  • 1Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260.

The Journal of Organic Chemistry
|October 24, 2001
PubMed
Summary

Researchers developed new fluorous tin reactants for Stille coupling reactions. This method enables efficient separation of products and reactants, simplifying synthesis and purification for fluorous organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Synthetic Chemistry

Background:

  • The Stille coupling is a widely used carbon-carbon bond-forming reaction.
  • Purification of reactants and products can be challenging in traditional Stille couplings.
  • Fluorous chemistry offers unique phase-separation properties for purification.

Purpose of the Study:

  • To introduce a novel class of fluorous aryl tin reactants for Stille coupling.
  • To demonstrate the efficient synthesis and purification of coupled products using fluorous techniques.
  • To optimize reaction conditions and explore the scope of this fluorous Stille coupling methodology.

Main Methods:

  • Synthesis of fluorous aryl tin compounds, specifically tris[(perfluorohexyl)ethyl]phenyl tin.

Related Experiment Videos

  • Stille coupling reaction between the fluorous tin reactant and bromobenzene using palladium catalysis.
  • Fluorous/organic liquid-liquid extraction for product and reactant separation.

    • Main Results:

    • Successful Stille coupling achieved with biphenyl in 90% yield from the organic phase.
    • Regeneration of the fluorous tin reactant (tris[(perfluorohexyl)ethyl]tin chloride) in >90% yield from the fluorous phase.
    • Optimization studies identified beneficial effects of LiCl and suppression of side products with CuI.

    Conclusions:

    • A novel and effective method for rendering tin reactants fluorous has been established.
    • This fluorous Stille coupling approach facilitates simplified purification and reactant recovery.
    • The methodology holds significant advantages for small- and large-scale synthesis, including automated synthesis.