Wednesday, June 25, 2008 - 11:00 AM
Federal Room B (Capital Hilton)
61

"Greening up" Organic Reactivity in the Undergraduate Laboratory: Aqueous Horner-Wadsworth-Emmons, Heck and Suzuki Reactions

Andrew P. Dicks, University of Toronto, Toronto, ON, Canada

There is currently significant interest in undertaking organic reactions under purely aqueous conditions, both in an academic and industrial climate. Water is the cheapest solvent on Earth; it has no flammability issues; it alleviates pollution problems associated with organic media and often engenders improved synthetic efficiency. The incorporation of three microscale synthetic experiments into the third-year organic chemistry undergraduate curriculum will be discussed. Each experiment involves usage of water as the solvent for a carbon-carbon bond forming process. Adoption of this approach facilitates synthesis of cinnamate ester sunscreen analogs via a Horner-Wadsworth-Emmons reaction and preparation of non-steroidal anti-inflammatory drug analogs via a Suzuki reaction (below), thus showcasing the "real-world relevance" aspect of organic chemistry to students.



Web Page: chemeducator.org/bibs/0012002/12070077ad.htm