Aryl-3-per(poly)fluoroacylindoles were synthesized in good yields by the 1,3-dipolar cycloaddition reaction of C-aryl-N-phenylnitrones with fluorine-containing olefins and the subsequent rearrangement of the adducts. An ionic mechanism was proposed for the formation of the titled compounds. Aryl-3-per (poly) fluoroacylindoles were synthesized in good yields by the 1,3-dipolar cycloaddition reaction of C-aryl-N-phenylnitrones with fluorine-containing olefins and the subsequent rearrangement of the adducts. Anionic mechanism was proposed for the formation of the titled compounds.