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A novel Pd-catalyzed cascade reaction of N , N -dialkyl-substituted o -alkynylanilines involving an indolization/ peri -C-H annulation/ N -dealkylation sequence has been developed to construct a cyclopenta-fused acenaphtho[1,2- b ]indole (ANI) scaffold. A variety of aromatic hydrocarbons having a peri -C-H bond at the alkynyl terminus, such as naphthalene, phenanthrene, pyrene, and fluoranthene, were employed, affording the corresponding π-extended ANI derivatives. The ANI molecules showed relatively narrow energy gaps by increasing HOMOs and lowering LUMOs, implying their potential applications as π-segments in low-band-gap materials.