ed400531w_si_004.pdf (1.93 MB)
Ligand-Free Suzuki–Miyaura Coupling Reactions Using an Inexpensive Aqueous Palladium Source: A Synthetic and Computational Exercise for the Undergraduate Organic Chemistry Laboratory
journal contribution
posted on 2015-12-17, 04:12 authored by Nicholas J. Hill, Matthew
D. Bowman, Brian J. Esselman, Stephen D. Byron, Jordan Kreitinger, Nicholas E. LeadbeaterAn 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.