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Organic synthesis in ionic liquids: the Stille coupling.

S T Handy1, X Zhang

  • 1Department of Chemistry, State University of New York at Binghamton, Binghamton, New York 13902-6000, USA. shandy@binghamton.edu

Organic Letters
|June 30, 2001
PubMed
Summary

The Stille coupling reaction was successfully performed in a recyclable ionic liquid solvent. This green chemistry approach allows for catalyst reuse, minimizing waste and maintaining high activity over multiple cycles.

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Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Catalysis

Background:

  • The Stille coupling is a vital carbon-carbon bond-forming reaction in organic synthesis.
  • Traditional Stille couplings often involve harsh conditions and generate significant waste.
  • Room-temperature ionic liquids (RTILs) offer potential for greener reaction media.

Purpose of the Study:

  • To investigate the efficacy of the Stille coupling reaction in a room-temperature ionic liquid (RTIL).
  • To evaluate the recyclability of the solvent and catalyst system.
  • To explore the influence of catalyst oxidation state on the reaction with different aryl halides.

Main Methods:

  • The Stille coupling reaction was conducted using 1-butyl-3-methylimidazolium tetrafluoroborate (BMIM BF4) as the solvent.

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  • The reaction mixture and catalyst were recycled for subsequent reaction cycles.
  • The activity of the recycled system was assessed over at least five uses.
  • The influence of the starting catalyst oxidation state was examined with aryl bromides and iodides.

    • Main Results:

    • The Stille coupling proceeded efficiently in the BMIM BF4 ionic liquid.
    • The solvent and catalyst system demonstrated excellent recyclability, with minimal loss of activity over five cycles.
    • A notable preference for the starting catalyst oxidation state was observed when using aryl bromides and aryl iodides.

    Conclusions:

    • 1-butyl-3-methylimidazolium tetrafluoroborate (BMIM BF4) is a suitable and recyclable medium for the Stille coupling reaction.
    • This methodology offers a greener alternative by enabling facile recycling of the solvent and catalyst.
    • Understanding catalyst oxidation state preferences can optimize Stille couplings with various aryl halides.