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Title of article :
ipso-Fluorination of aryltrimethylsilanes using xenon difluoride
Author/Authors :
Aileen P. Lothian، نويسنده , , Christopher A. Ramsden، نويسنده , , Maxine M. Shaw، نويسنده , , Rachel G. Smith، نويسنده ,
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هفته نامه با شماره پیاپی سال 2011
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Abstract :
Reaction of aryltrimethylsilanes with xenon difluoride in C6F6/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 CH2Cl2/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→Pyrexδ−] followed by ligand coupling are discussed.
Keywords :
aryl fluorides , Electrophilic fluorination , Xenon difluoride , hypervalent , Arylsilanes
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