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The First Organosilver(III) Fluoride, [PPh4 ][(CF3 )3 AgF].

Daniel Joven-Sancho1, Miguel Baya1, Antonio Martín1

  • 1Instituto de Síntesis Química y Catálisis Homogénea (iSQCH), CSIC-Universidad de Zaragoza, C/ Pedro Cerbuna 12, 50009, Zaragoza, Spain.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 28, 2019
PubMed
Summary

Researchers synthesized a novel organosilver(III) fluoride complex, [(CF3 )3 AgF][PPh4 ], for fluorination reactions. This study details its isolation, stability, and reactive Ag-F bond characteristics.

Keywords:
fluorideshigh oxidation stateorganosilver(III)thiolstrifluoromethylation

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Area of Science:

  • Organometallic Chemistry
  • Fluorination Chemistry
  • Coordination Chemistry

Background:

  • Organosilver(III) fluoride complexes are implicated in fluorination processes.
  • These complexes have not been previously isolated or detected.
  • The synthesis and characterization of such species are of significant interest.

Purpose of the Study:

  • To report the successful synthesis and isolation of a novel organosilver(III) fluoride complex.
  • To investigate the stability and reactivity of the silver-fluorine (Ag-F) bond in this new compound.
  • To explore the potential of this complex in fluorination chemistry.

Main Methods:

  • Synthesis of the trifluoromethyl derivative [PPh4 ][(CF3 )3 AgF].
  • Isolation of the complex in high yield.
  • Thermodynamic stability assessment using computational methods and multistage mass spectrometry (MSn) with collision-induced dissociation (CID).
  • Structural characterization via X-ray crystallography.

Main Results:

  • Successful synthesis and isolation of [PPh4 ][(CF3 )3 AgF] in high yield.
  • Computational and MSn/CID data confirm the thermodynamic stability of the Ag-F bond.
  • X-ray crystallography reveals significant elongation of the Ag-F bond, indicating a nucleophilic character of the fluoride ligand.
  • The Ag-F bond demonstrates reactivity, undergoing hydrolysis and solvolysis with thiols.

Conclusions:

  • The first isolation of an organosilver(III) fluoride complex, [PPh4 ][(CF3 )3 AgF], has been achieved.
  • The Ag-F bond exhibits notable stability yet possesses significant nucleophilic character and reactivity.
  • This compound represents a potentially valuable reagent for fluorination applications.