4th Annual WML Academic Symposium

Recently, a homogeneous catalyst system utilizing copper(I) bromide, bipyridine, TEMPO (2,2,6,6-tetramethylpiperidine-N-oxyl), and N-methylimidazole (NMI) to oxidize primary alcohols to the corresponding aldehydes was reported. Acetonitrile and acetone were used as the solvents in these initial studies. The creators of the copper(I)/TEMPO system reported the rate-limiting step of this oxidation reaction to be slower than comparable literature values, attributing this discrepancy to solvent and ligand effects. The results of this oxidation reaction with a variety of benzylic alcohols in a variety of solvents will be reported. Baseline reaction times and yields were performed in acetonitrile and acetone for comparison. The purity of the aldehydes produced by this catalyst system was evaluated by IR and NMR spectroscopy.