Resumen de Breaking Amide C–N Bonds in an Undergraduate Organic Chemistry Laboratory
Jacob E. Dander, Lucas A. Morrill, Melinda M. Nguyen, Shuming Chen, Neil K. Garg
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.
