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CF Activation of Fluorobenzene by Silylium Carboranes: Evidence for Incipient Phenyl Cation Reactivity
- Duttwyler, Simon;
- Douvris, Christos;
- Fackler, Nathanael LP;
- Tham, Fook S;
- Reed, Christopher A;
- Baldridge, Kim K;
- Siegel, Jay S
Published Web Location
https://doi.org/10.1002/anie.201003762Abstract
Si(mply) rips it apart: CF 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).
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