Breaking Amide C-N Bonds in an Undergraduate Organic Chemistry Laboratory

An undergraduate organic chemistry laboratory experiment involving the breakage of amide C-N bonds is reported. Whereas amides are typically considered stable species due to well-established resonance effects, this experiment allows students to cleave the amide C-N bond in a nickel-catalyzed esterification process. Moreover, students perform the experiment on the benchtop using a commercially available paraffin wax capsule containing the necessary nickel precatalyst and N-heterocyclic carbene ligand. The laboratory procedure introduces students to several modern topics in organic chemistry that are not otherwise well-represented in typical undergraduate organic chemistry curricula, such as amide bond cleavage, transition metal-catalyzed cross-coupling reactions, and nonprecious-metal catalysis.