Dander Jacob E, Morrill Lucas A, Nguyen Melinda M, Chen Shuming, Garg Neil K
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
J Chem Educ. 2019 Apr 9;96(4):776-780. doi: 10.1021/acs.jchemed.8b00489. Epub 2019 Mar 6.
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 -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.
报道了一个涉及酰胺C-N键断裂的本科有机化学实验室实验。鉴于酰胺由于已确立的共振效应通常被认为是稳定的物种，但该实验使学生能够在镍催化的酯化过程中裂解酰胺C-N键。此外，学生在实验台上使用含有必要镍预催化剂和杂环卡宾配体的市售石蜡蜡胶囊进行实验。该实验步骤向学生介绍了有机化学中的几个现代主题，这些主题在典型的本科有机化学课程中没有得到很好的体现，例如酰胺键裂解、过渡金属催化的交叉偶联反应和非贵金属催化。
