Herein, we report a visible-light-induced, palladium-catalyzed desaturation/sulfonation cascade, offering a concise route to a series of highly valuable 4-sulfonyltetrahydropyridine scaffolds from inexpensive and readily available piperidine derivatives with sodium sulfinates. The key to the success of this transformation is the well-designed sequence of palladium-mediated 1,5-hydrogen atom transfer/β-hydride elimination/allylic sulfonation process, which demonstrates the synthetic potentials for orchestrating synthetic events by rationally taking advantage of varied catalytic modes.