Abstract: The Bahamonde group harnesses the distinct one-electron chemistry and photochemical reactivity of Ni complexes to generate and trap C-centered radicals enantioselectively and promote C−N reductive eliminations at room temperature. Our excitement for studying these systems stems from the fact that these two apparently unrelated processes are facilitated under almost identical conditions, but to date the ligand features, photocatalyst properties, and subtle reaction condition variations that favor one pathway over the other are not yet understood. Additionally, to expedite reaction optimization, the group develops multivariate linear regression models correlating observed enantioselectivity to computed molecular descriptors.