The increasing number of heterocyclic natural products and the well-known applications of heterocyclic chemistry to pharmaceutical research dictate the development of new synthetic methods for accessing heterocycles. More specifically, there has been a recent surge in the development of methods to access tryptamine derived cores, whose bioactivity and applications have been hindered by extremely low natural production rates and inefficient synthetic methods. This structural core is present in numerous natural products and biologically active molecules that exhibit a variety of properties such as anti-leukemia activity, as well as inhibiting colon and lung cancer. We have developed a novel method that is promising in its ability to access a diverse array of these pharmaceutically relevant motifs in a simple, atom efficient manner. By taking advantage of the copper-mediated dimerization radical formation to insert a nitroso group, we aim to simultaneously yield two products, the amino and oxy tryptamine derivatives for further pharmaceutical investigation.