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The Tris(pentafluoroethyl)silanide Anion.

Nico Schwarze1, Simon Steinhauer1, Beate Neumann1

  • 1Universität Bielefeld, Fakultät für Chemie, Centrum für Molekulare Materialien, Universitätsstrasse 25, 33615, Bielefeld, Germany.

Angewandte Chemie (International Ed. in English)
|December 1, 2016
PubMed
Summary
This summary is machine-generated.

Tris(pentafluoroethyl)silane is a versatile reagent for hydrosilylation reactions, yielding specific products based on the alkyne used. It can also form a stable silanide ion, enabling new chemical transformations.

Keywords:
fluorinehydrosilylationperfluoroalkyl compoundssilanessilanides

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Area of Science:

  • Organosilicon Chemistry
  • Fluorine Chemistry
  • Catalysis

Background:

  • Tris(pentafluoroethyl)silane is synthesized from Si(C2F5)3X (X=Cl, Br) and Bu3SnH.
  • Organosilanes are important reagents in organic synthesis.

Purpose of the Study:

  • To explore the reactivity of tris(pentafluoroethyl)silane in hydrosilylation reactions.
  • To investigate the formation and stability of the tris(pentafluoroethyl)silanide ion.

Main Methods:

  • Hydrosilylation reactions catalyzed by palladium.
  • Deprotonation of tris(pentafluoroethyl)silane using sterically demanding bases.
  • Isolation and characterization of the silanide ion using crown ethers or cryptands.

Main Results:

  • Hydrosilylation of phenylacetylene with tris(pentafluoroethyl)silane yielded the alpha-addition product.
  • Hydrosilylation of trimethylsilylacetylene afforded the beta-trans product.
  • Tris(pentafluoroethyl)silanide ion was generated and isolated as a salt at room temperature.

Conclusions:

  • Tris(pentafluoroethyl)silane is a valuable reagent for regioselective hydrosilylation.
  • The corresponding silanide is stable and isolable, opening avenues for further synthetic applications.