Iron-Based Tandem Catalysis: From Petroleum toward Pharmaceutical Laboratories for Organic Undergraduate Students─Product Identification by TLC and 1H NMR

Abstract

Catalysis and catalytic cycles are widely used in both research and industry. The addition of a catalysis experiment into the undergraduate laboratory curriculum is important and necessary training to expand student learning. Here, an experiment demonstrating iron-based tandem catalysis was developed and implemented in an organic chemistry course for second-year and upper-division undergraduate students at Mississippi State University. The experiment uses TLC and 1H NMR to track the reaction and identify the core pharmaceutical structure produced during the experiment. Reactions contained inside the catalytic cycles include iminium generation, imino-ene condensation, and aza-Prins reaction. The catalytic cycle approach allows for a decrease in time for reaction, chemicals, and waste produced. This experiment was successfully tested over two semesters (110 students) at a major university. Learning objectives were met to support student understanding of catalytic cycles and reaction mechanisms. This laboratory experiment provided hands-on experience using TLC and 1H NMR to identify a core structure of pharmaceutical compounds produced from petroleum.