Abstract: Heterocyclic scaffolds are present in greater than 85% of biologically active compounds. Metalated heterocycles, such as borylated and silylated heterocycles, are of interest because they enable the synthesis of diversely functionalized heterocycles, through the cross-coupling, conjugate addition, and oxidation reactivity of their metal–carbon bonds. Therefore, development of synthetic methods for the generation of metalated heterocycles has garnered significant attention.