University Honors

Carbon-nitrogen (C-N) couplings have an essential role in the production of commodity chemicals. For example, 84% of drugs contain at least one nitrogen atom, with amines and amides being the most common functional groups, and 59% incorporating nitrogen-containing heterocycles. Based on previous literature, C-N cross-coupling has been extensively accomplished through palladium (Pd) and nickel (Ni) catalysis which present high costs. This research focuses on developing a new methodology for amine N-arylation with an inexpensive copper (Cu)-indole system as catalyst under photochemical conditions. Through multiple chemical experiments in which various laboratory techniques are utilized, a set of conditions have been tested to identify the optimal conditions for increasing product yield. Each reaction parameter like temperature, concentration, and stoichiometry was investigated in separate experiments to determine their effect on product formation. The project also explores the role and optimal structure of the indole ligand in the reaction. This optimized reaction is useful in the pharmaceutical industry utilizing a C-N bond between an aryl and an amine during medicinal drug making.