Having confirmed promising results for our generator module, we proceeded to evaluate the reactivity of the anionic species through a leaving group assessment (Scheme 1, Leaving group assessment). The results indicated the need for effective nucleofuges for the reaction to proceed successfully. In the case of the benzyl benchmark substrate, chloride, acetate, trifluoroacetate, and Katrizky salt electrophiles failed to yield the desired product. However, bromide, iodide, mesylate, and tosylate derivatives proved to be competent substrates towards the formation of product 4 in good to excellent yields (59-98%). Regarding the n-hexyl substrate, iodide-bearing substrates underwent satisfactory substitution in the presence of silver triflate, resulting in the formation of alkyl amine 5, while bromide, mesylate, and tosylate variants still provided the target product in quantities suitable for medicinal chemistry applications.