We began our synthetic investigations with phenol as a model nucleophile due to its limited occurrence in nickel photoredox or lack of examples in metal-electrocatalytic protocols. We reasoned in our previous report that alcohols showed low reactivity with cyclohexylamine because their access to the coordination sphere of nickel is hindered by the competitive binding of the more nucleophilic cyclohexylamine. Given that nucleophile coordination is essential for acidification and subsequent deprotonation with a weak base, we aimed to identify a primary alkyl amine that could enhance nickel's inherent coordination lability, thus facilitating ligand exchange while maintaining sufficient reactivity towards oxidative addition (Table ).