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C[BOND]F Activation of Fluorobenzene by Silylium Carboranes: Evidence for Incipient Phenyl Cation Reactivity


  • We gratefully acknowledge the University of Zurich, the Swiss National Science Foundation and the US National Science Foundation (CHE 084428) for financial support. We thank Dr. Thomas Fox (UZH) for the measurement of NMR spectra and Dr. Evgenii S. Stoyanov (UCR) for the measurement of IR spectra.


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Si(mply) rips it apart: C[BOND]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).