Breaking Amide C–N Bonds in an Undergraduate Organic Chemistry Laboratory
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Jacob E. Dander [1] ; Lucas A. Morrill [1] ; Melinda M. Nguyen [1] ; Shuming Chen [1] ; Neil K. Garg [1]
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[1] University of California, United States
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- Localización: Journal of chemical education, ISSN 0021-9584, Vol. 96, Nº 4, 2019, págs. 776-780
- Idioma: inglés
- Texto completo no disponible (Saber más ...)
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Resumen
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.
