The synthesis of valuable 2a,3-dihydrobenzo[cd]indolines was successfully achieved by combining IPr-Pdcycle-OxaNaphthyl-catalyzed cross-coupling and proton-induced hydroarylation in a one-pot method. In situ-generated alkynyl-functionalized 3,3-disubstituted indolines were proved as the key intermediate, bearing a broad scope of substrates with diverse functional groups and electronic properties.