Herein, the palladium-catalyzed autotandem reaction of cyclopropyl alcohols with gem-dibromoolefins is described. This reaction system involves two distinct mechanistic processes, both efficiently catalyzed by the same palladium catalyst. This approach accommodates a wide substrate scope using readily available starting materials, offering a new and efficient method for synthesizing a series of β-pyrrolo[1,2-a]quinolinyl ketones.