Ligand-Free Suzuki−Miyaura Coupling Reactions Using an Inexpensive Aqueous Palladium Source: A Synthetic and Computational Exercise for the Undergraduate Organic Chemistry Laboratory

Author(s): 
Hill, N,J.; Bowman, M.D.; Esselman, B.J.; Byron, S.D.; Kreitinger, J.; Leadbeater, N. E.
Author Affiliation: 
Department of Chemistry, University of WisconsinMadison, Madison, Wisconsin 53706-1322, United States
Journal: 
Journal of Chemical Education
Year: 
2014
Volume: 
91
Pages: 
1054-1057
Abstract: 

An inexpensive procedure for introducing the Suzuki–Miyaura coupling reaction into a high-enrollment undergraduate organic chemistry laboratory course is described. The procedure employs an aqueous palladium solution as the catalyst and a range of para-substituted aryl bromides and arylboronic acids as substrates. The coupling reactions proceed rapidly at room temperature using standard glassware and do not require ligands, an inert atmosphere, or specialized equipment. Computational chemistry is used to explore the molecular and electronic structures of typical starting materials and products of the Suzuki–Miyaura coupling.

Abstract reproduced with permission. Copyright: 
American Chemical Society
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