Reaction Optimization. At the outset of the study, we were particularly interested in exploiting aryl boronic acids as arylating reagents, given that they represent a large class of commercially available stable aryl building blocks. Given the significance of cyanoalkyl motifs in medicinal chemistry, 20 we considered using oximes as precursors to cyanoalkyl radicals given their ease of preparation. It is important to note that our previous work has demonstrated photoinduced copper-catalyzed radical cross-coupling of benzylic radicals with boronic acids; 21 however, this strategy is restricted to achiral 2,2'-bipyridyl-type ligand for catalytic activity.