The development of general approaches for the regioselective construction of propargylic derivatives from propargylic electrophiles remains a formidable challenge in synthetic chemistry. Enabled by the newly developed propiolate-enabled C−N activation, we disclosed an efficient palladium-catalyzed deaminative Hiyama coupling of propargylamines with aryl silanes under microwave irradiation. Various structurally diverse propargyl derivatives are produced in good to excellent yields, utilizing propargylamines as propargylic electrophiles in which C−N bond was activated by in situ formed propargylic ammonium salts. The salient features of this protocol include readily or easily available feedstock, broad substrate scope, single-step preparation, and high regioselectivity.