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

ABSTRACT: 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.

SUBMITTER: Dander JE

PROVIDER: S-EPMC6502258 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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

Dander Jacob E JE Morrill Lucas A LA Nguyen Melinda M MM Chen Shuming S Garg Neil K NK

Journal of chemical education 20190306 4

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 <i>N</i>-heterocyclic car ...[more]

PMID: 31073247

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