Journal
JOURNAL OF CHEMICAL EDUCATION
Volume 91, Issue 7, Pages 1054-1057Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ed400531w
Keywords
Second-Year Undergraduate; Laboratory Instruction; Organic Chemistry; Hands-On Learning/Manipulatives; Inquiry-Based/Discovery Learning Catalysis; Green Chemistry; Molecular Modeling Organometallics
Funding
- UW-Madison Instructional Laboratory Modernization (ILM) program
- Madison Initiative for Undergraduates (MIU)
- National Science Foundation [CHE-0840494]
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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.
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