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

  • Author(s): Duttwyler, Simon;
  • Douvris, Christos;
  • Fackler, Nathanael LP;
  • Tham, Fook S;
  • Reed, Christopher A;
  • Baldridge, Kim K;
  • Siegel, Jay S
  • 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-C6H 3)SiMe2] + paired with the anion CHB 11Cl11-. 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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