A Pd/phase-transfer catalyst cooperatively catalyzed domino Heck/allylation reaction is first reported, which represents interesting substrate-dependent regioselectivity. Under the same conditions, Ts-protected N-(2-iodophenyl)allenamides produced only linear allylation products, while Cbz, Ac, or Boc-protected N-(2-iodophenyl)allenamides and N-(2-iodobenzoyl)allenamides with various compounds generated branch allylation products with an exocylic C═C bond and two vicinal stereocenters. Up-scale syntheses and diverse fused cyclization transformations of products were then carried out. The enantioselective version for the domino process was studied.