Synthesis of organocobalt complexes for the catalytic preparation of substituted-pyridines

CHED 280

Eric J Hawrelak, ehawrela@bloomu.edu and Sarah E. Leshinski, seleshin@bloomu.edu. Department of Chemistry, Bloomsburg University of Pennsylvania, 400 E Second St, Hartline Science Center, Bloomsburg, PA 17815
The catalytic synthesis of substituted pyridines via a cyclotrimerization reaction has been extensively studied over the last 60 years. However, a lot of this research has been focused on a narrow range of target molecules. More fundamental studies of electronic and steric effects on the outcome of alkyne/nitrile cyclotrimerization is needed. It has been demonstrated in the literature that electron-deficient metal centers have higher catalytic activity, while sterically hindered complexes are more regioselective. The focus of this project is to investigate the activity and regioselective synthesis of substituted pyridines using a series of pentafluorophenyl-substituted cyclopentadienyl cobalt complexes. We have prepared a pentafluorophenyl-substituted cyclopentadienyl ligand, (C6F5)Cp and used it to prepare the desired organocobalt complex, [(C6F5)CpCo(CO)2. The cobalt complex was characterized using 1H, and 19F NMR as well as infrared spectroscopy. Based upon literature precedent, the varying electronic nature and steric bulk of each ligand is expected to demonstrate interesting trends in both the activity of the catalyst and regioselectivity of the pyridine produced.