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C-F activation of fluorobenzene by silylium carboranes: Evidence for incipient phenyl cation reactivity

  • Author(s): Duttwyler, S
  • Douvris, C
  • Fackler, NLP
  • Tham, FS
  • Reed, CA
  • Baldridge, KK
  • Siegel, JS
  • et al.
Abstract

Si(mply) rips it apart: C-F activation of fluorobenzene has been achieved using the extremely strong silyl Lewis acids [Et3Si(X)]+(X=PhF or Et3SiH) and [(2,6-dixylyl-C6H3)SiMe2]+paired with the anion CHB11Cl11-. They abstract fluoride from unactivated fluorobenzene to give arylated products, consistent with phenyl-cation-like reactivity (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

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