1315574-15-2Relevant academic research and scientific papers
Ipso-Fluorination of aryltrimethylsilanes using xenon difluoride
Lothian, Aileen P.,Ramsden, Christopher A.,Shaw, Maxine M.,Smith, Rachel G.
experimental part, p. 2788 - 2793 (2011/05/02)
Reaction of aryltrimethylsilanes with xenon difluoride in C 6F6/Pyrex at room temperature gives aryl fluorides in good yield. The reaction is inhibited when acetonitrile is used as solvent but proceeds well in CFCl3/Pyrex or CH 2Cl2/Pyrex. Pyrex appears to be a very effective heterogeneous catalyst for this ipso-fluorination. The reaction does not proceed in PTFE, quartz, soda glass or glassy-carbon flasks or Pyrex flasks pre-rinsed with 2 M NaOH. Aryltrimethylstannanes and arylboronic acids and their esters do not undergo ipso-fluorination under similar conditions. Plausible mechanisms involving electrophilic addition of polarised xenon difluoride [FXeδ+?F→Pyrex δ-] followed by ligand coupling are discussed.
