Introducing Undergraduates to Research Using a Suzuki–Miyaura Cross-Coupling Organic Chemistry Miniproject

Abstract

A five-week miniproject is described for an upper-division experimental organic chemistry course. The activities include synthesis of a phenylboronic acid via a Grignard reaction and its use in a Suzuki−Miyaura crosscoupling reaction. Technical skills and concepts normally presented in practical organic chemistry courses are covered, including the use of an inert atmosphere (Schlenk tube technique), separation of mixtures (filtration), melting range determination, infrared (IR) spectrum, stoichiometric calculations and gas chromatography techniques.

Exploring the Effect of Phosphine Ligand Architecture on a Buchwald–Hartwig Reaction: Ligand Synthesis and Screening of Reaction Conditions

“…Palladium-catalyzed coupling reactions are fundamental methods in synthetic organic chemistry . Introductory-level textbooks have recently begun to include discussion of this area, and many instructional laboratory exercises are now available for showcasing the Suzuki–Miyaura coupling − and related reactions. − In contrast to these C–C σ-bond forming processes, the Pd-catalyzed coupling of amines with organic halides to form C–N σ-bonds, termed the Buchwald–Hartwig amination (BHA), is underrepresented in the instructional literature. Indeed, despite its broad utility, − only three instructional laboratory modules focusing on the BHA reaction have been reported.…”

One-Pot Suzuki–Miyaura C–C Coupling Reaction versus Stepwise Reaction Involving Isolated Synthesized Catalyst Addition

“…Michael Novak et al also reported a research project based on the Suzuki–Miyaura cross-coupling reaction that involved an entirely aqueous reaction solvent, and the easily recovered and nontoxic Pd/C catalyst. There are other reports in the literature in which experiments were designed to demonstrate the coupling reactions in multistep syntheses …”

Integrating Green Chemistry into Teaching Laboratories: Aqueous Suzuki–Miyaura Cross-Coupling Reaction Using a Recyclable Fluorous Precatalyst

“…Several articles published in this Journal have described greener modifications of the Suzuki–Miyaura cross-coupling reaction. − These include replacing palladium with nickel; − employing a microwave-assisted reaction condition; using an aqueous organic solvent, − ionic liquid, or water , as the reaction solvent; and synthesizing boronic acid via the Grignard route to obtain the starting material …”