Ligand-free suzuki-miyaura coupling reactions using an inexpensive aqueous palladium source: A synthetic and computational exercise for the undergraduate organic chemistry laboratory

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. © 2014 The American Chemical Society and Division of Chemical Education, Inc.