The reaction optimization was initiated using conditions very similar to those reported for Fe catalyzed amine α-C-H oxygenation. The one major difference we introduced for amine α-C-H cyanation was the departure from pyridine as a solvent to avoid incompatibilities caused by potential base sensitivities of complex substrates. Tri-n-butylamine (1) was chosen as a test substrate, as its α-C-H bonds do not exhibit additional activation (i.e., benzylic or in aniline-type C-H bonds). We reasoned that establishing the desired reactivity with the unactivated substrate 1 should in turn also enable C-H functionalizations of anilines and benzylic amines, and thus provide a general reaction protocol.