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Keywords:

  • allyl cations;
  • arenes;
  • carboranes;
  • hyperconjugation;
  • silyl cations

Abstract

Thumbnail image of graphical abstract

Sly silyl caught in the act: Protonation of a mesitylene ring by the strongly acidic arenium carborane [CH3C6H6]- [CHB11Me5Br6] initiates a cascade reaction that results in a stable β-silyl allyl cation (see picture, H yellow, C blue, silyl allyl group red). Remarkably, the driving force in the reaction suffices to disrupt a stable aromatic ring in favor of a cationic reactive intermediate.