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Anhydrous tetrabutylammonium fluoride.

Haoran Sun1, Stephen G DiMagno

  • 1Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska 68588-0304, USA.

Journal of the American Chemical Society
|February 17, 2005
PubMed
Summary
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Tetrabutylammonium fluoride (TBAF) is synthesized via nucleophilic aromatic substitution. This stable fluoride salt resists Hofmann elimination in anhydrous polar aprotic solvents but decomposes in protic solvents.

Area of Science:

  • Organic Chemistry
  • Fluoride Chemistry

Background:

  • Tetrabutylammonium fluoride (TBAF) is a crucial reagent in organic synthesis.
  • Previous understanding suggested TBAF instability under certain conditions.

Purpose of the Study:

  • To develop a novel low-temperature synthesis for Tetrabutylammonium fluoride (TBAF).
  • To investigate the stability and reactivity of TBAF under various solvent conditions.

Main Methods:

  • Synthesis of TBAF through nucleophilic aromatic substitution of hexafluorobenzene with tetrabutylammonium cyanide.
  • Water scavenging using in-situ generated hexacyanobenzene.
  • Stability studies of TBAF in polar aprotic and hydroxylic solvents.

Main Results:

  • Successful low-temperature preparation of TBAF.

Related Experiment Videos

  • TBAF demonstrated unexpected stability towards Hofmann elimination in anhydrous polar aprotic solvents.
  • Hydroxylic solvents were found to catalyze both TBAF decomposition and proton exchange with DMSO.

    • Conclusions:

    • A new, efficient method for TBAF synthesis was established.
    • The stability profile of TBAF was clarified, highlighting its robustness in anhydrous non-protic media.
    • Understanding TBAF's reactivity with protic solvents is crucial for its effective application.