1,6-Enynes react with aryl and heteroaryl halides via a [2+2+2]- process to furnish bicyclic products in moderate to good yields. In some cases the alkylpalladium(II) intermediate can be diverted to a [1+2]-process furnishing cyclopropanes or to a cyclohexene derivative. The cascade process is initiated by regiospecific carbopalladation of the enyne by the aryl- or heteroaryl-palladium (II) halide.