CLAS: Colby Liberal Arts Symposium

Synthesis and Characterization of a Copper(I)-phenyl Complex

Parker-Reed, SSWAC

Compounds or complexes combining an organic species and a copper ion are amongst the most widely used organometallic reagents in synthetic organic chemistry. However, the chemistry for such organocopper compounds is underdeveloped including that for copper(I)-arene complexes, which are quite rare. Nonetheless, once the chemical properties of such copper-arene complexes are better understood, it will be easier to find uses for them, for instance as catalysts. Previous work on this project has produced evidence that copper(I)-arene complexes bearing phenyl and naphthyl groups behave differently from one another in arene replacement reactions. Thus, the phenyl does not seem to bind as strongly to the copper ion as the naphthyl in solution and also the data have suggested that the binding site of the copper ion to the phenyl and the naphthalene group might be different. Hence, the goal of this project is to synthesize and characterize new copper(I) complexes with large ring (macrocyclic) ligands that have appended arene groups (phenyl, naphthyl) in order to probe the factors that contribute to the strength and selectivity of the copper-arene bond. This project is performed in collaboration with Max Cushner, who is studying a copper(I)-naphthyl complex whereas I am targeting the copper(I)-phenyl complex. The synthesis of the macrocyclic ligand with an appended ethyl phenyl group requires four steps, and another two steps are needed to make the target Cu(I)-phenyl complex. Some of these steps require oxygen-and/or water free conditions, necessitating the use of special synthetic techniques. The properties of the target complex will be studied using a variety of characterization techniques and the progress towards this synthesis will be discussed.

https://digitalcommons.colby.edu/clas/2014/program/283