Resumen de Discovering Green, Aqueous Suzuki Coupling Reactions: Synthesis of Ethyl (4-Phenylphenyl)acetate, a Biaryl with Anti-Arthritic Potential
Nancy E. Costa, Andrea L. Pelotte, Joseph M. Simard, Christopher A. Syvinski, Amy M. Deveau
Suzuki couplings are powerful chemical reactions commonly employed in academic and industrial research settings to generate functionalized biaryls. We have developed and implemented a discovery-based, microscale experiment for the undergraduate organic chemistry laboratory that explores green Suzuki coupling using water as the primary solvent. This experiment exposes students to the professional responsibilities of a pharmaceutical chemist and promotes a problem-solving approach toward learning green chemistry principles. Specifically, students assume the role of a medicinal chemistry researcher striving to identify the greenest and most cost-effective method out of three proposed synthetic approaches to make ethyl (4-phenylphenyl)acetate. Ethyl (4-phenylphenyl)acetate is a precursor to the drug felbinac and demonstrates promise as a lead compound in the discovery of new nonsteroidal anti-inflammatory drugs for the treatment of arthritis.
