The coupling with loratadine demonstrates the applicability of our method in late-stage functionalization and it was particularly encouraging that we saw no transesterification due to the mild nature of our conditions. Though electron rich aryl chlorides, such as N-Boc-5-chloroindole, were unsuccessful under our conditions (<10% crude yield), likely due to slow oxidative addition, we were able to couple the highly electron rich 5-bromo-1,2,3-trimethoxybenzene to yield 5 in 64% yield. Lastly, the coupling with benzyl amine instead of benzyl alcohol to yield 6 (35%) demonstrates that our new conditions do not prevent reactivity with other nucleophiles. However, the coupling with benzyl mercaptan was unsuccessful, which we believe arises from thiol deprotonation by DBU and the resulting thiolate altering the Ni speciation. Though the new conditions inhibited reactivity with thiols, the ability to turn on chloride reactivity and maintain amine reactivity demonstrates how utilizing mechanistic insights can improve reaction scope in dual photoredox/Ni catalyzed couplings.