Catalytic C-H Arylation of Unactivated C-H Bonds by Silylium Ion-Promoted C(sp2)-F Bond Activation

Silylium ions facilitate the catalytic direct cross coupling of aryl fluorides with simple arenes and alkanes. This C-H arylation approach is initiated by silylium ion-mediated fluoride abstraction, which is followed by Friedel Crafts or C-H insertion reactions of the resulting phenyl cation equivalents. An o-silyl group in the fluoroarene substrate is the key for selective intermolecular transformations, stabilizing the aryl cation intermediate and serving as an internal silylium ion precursor.