We report a novel organocatalytic one-pot cascade bromination-Michael-type Friedel-Crafts alkylation dearomatization-nucleophilic rearrangement aromatization cascade process for the direct α-indolylation of unfunctionalized enals from readily available indoles with good yields and high E selectivity. The simplicity and practicality of its high efficiency for formation of a new C(sp(2))-C(sp(2)) bond constitute the most attractive advantage of this reaction.