A palladium-catalyzed tandem reaction is reported that involves chloropalladation/cyclization and dearomative cyclization to construct a tricyclic bridged [3.2.1] carbocyclic-skeleton and oxa- and aza-skeletons. In this domino process, a level of ring strain and other competitive reactions, i.e., protonolysis, β-hydride elimination, and chlorination of the C-Pd bond, were suppressed to the lowest level under mild reaction conditions.