Discovering Green, Aqueous Suzuki Coupling Reactions: Synthesis of Ethyl (4-Phenylphenyl)acetate, a Biaryl with Anti-Arthritic Potential

• Autores: Nancy E. Costa, Andrea L. Pelotte, Joseph M. Simard, Christopher A. Syvinski, Amy M. Deveau
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 89, Nº 8, 2012, págs. 1064-1067
• Idioma: inglés
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• Resumen

  • 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.