Successful substrates include triclopidine 18, gramine 19, and gefitinib 23 with heterocyclic substructures that remain untouched; terbinafine 21 and amitriptyline 17, whose structures incorporate double and triple bonds; as well as venlafaxine 24 with an unprotected tertiary alcohol moiety. Additional functionalities that are tolerated are ethers (in diphenhydramine, 20), amides (in lidocaine, 22), and oxidizable/electron-rich arene groups (in lidocaine, 22, gefitinib, 23, and imipramine, 26). In all cases, the obtained assay yields are above 50%, which is impressive for a protocol that was initially optimized with the entirely unfunctionalized substrate NBu 3 (1). This study demonstrates that breadth of functional groups tolerated is significantly improved when comparing the herein described protocol with photoredox-driven α-C-H cyanations, the thus far mildest protocol to achieve an analogous tranformation.