Finally, the robustness of the reaction was tested on a gram scale with the preparation of piperidine 13 from sulfonylhydrazide 11 and aryliodide 12. Without any modification to the general protocol the reaction proceeded well to deliver adduct 13 in 50% isolated yield and 84% e.s.. Since it is well known in process chemistry that enantioenriched materials are easily upgraded via recrystallization, the Cbz group was removed and after a single round of recrystallization (using complex 72, and the stereoretentive cycle is closed by oxidative addition of 12 to 72, returning complex 66. Because of the rapid nature of this radical rebound and the proximity of the active atoms, the stereochemistry is retained. As described in the Supplemental Materials, additional pathways were also considered but found to be unlikely (e.g., the possibility for a sulfonylhydrazide-assisted Ni(I)/Ni(III) cycle).