Next, we tested whether halogenating Zincke imine intermediates could outcompete neighboring electron-rich aromatic rings and whether dihalogenation processes were feasible. As shown in Figure , pyridines are iodinated exclusively over thiophenes, furans, anisoles, and phenoxy groups (43-46). Similarly, iodination occurs on the pyridine in fused ring systems such as azafurans, protected azaindoles, and azathiophenes that conventionally react at the fivemembered heterocyclic portion (47-50) . Figure also shows that C-Hal bond formation can be sequenced to form 3,5-dihalogenated pyridines, a motif with two orthogonal vectors for further synthetic transformations . Although a one-pot procedure was unsuccessful, we could isolate Zincke imines 3-I and 3-Br, and subjected them to a second round of halogenation, resulting in various permutations of dihalopyridines 51-56. We formed dichloropyridine 57 directly from Zincke imine 2e by modifying conditions C to include 2.05 equivalents of NCS.