A novel and straightforward methodology for palladium-catalyzed carbopalladation-initiated domino carbonylative cyclization to construct bisheterocycles has been established. With TFBen as an efficient and convenient CO source, the protocol is capable of generating oxindole and 3-acylbenzofuran/3-acylindole moieties from the corresponding N-(o-iodoaryl)acrylamides and o-alkynylphenols/o-alkynylanilines with the formation of three C-C bonds and one C-O/C-N bond in a single one-step operation. A wide range of bisheterocycles bearing oxindoles and 3-acylbenzofurans/3-acylindoles were prepared in moderate to excellent yields with good functional group tolerance.