The oxidative dearomatization of para-substituted o-alkynylanilines afforded 2-alkynyl cyclohexadienimines, which can act as active substrates for reaction with electron-rich styrenes. The reaction is metal-controlled. Bi(OTf)3-catalyzed reactions afforded 3,4-dihydro-cyclopenta[c,d]indoles, and AgOTf-catalyzed reactions provided tricyclic pyrrole derivatives.