Divergent reactions of various 1-(aminoalkyl)naphthols and 2-(aminoalkyl)phenols (commonly known as Betti bases) with indoles under Brønsted acid catalysis is reported. With the reaction strategies, one can efficiently synthesize important indole derivatives such as 3-(α,α-diarylmethyl)indoles and chromeno [2,3-b]indoles. Furthermore, we disclose here a new C-C bond-cleavage reaction, in which naphthol and phenol behave as leaving groups to produce diarylmethanes.