ipso-Fluorination of aryltrimethylsilanes using xenon difluoride

AP Lothian, CA Ramsden, MM Shaw, RG Smith

Index: Lothian, Aileen P.; Ramsden, Christopher A.; Shaw, Maxine M.; Smith, Rachel G. Tetrahedron, 2011 , vol. 67, # 15 p. 2788 - 2793

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Citation Number: 10

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 2M ...