So Sonia S, Oottikkal Shameema, Badjić Jovica D, Hadad Christopher M, Mattson Anita E
Department of Chemistry and Biochemistry, 100 West 18th Avenue, The Ohio State University , Columbus, Ohio 43210, United States.
J Org Chem. 2014 Jun 6;79(11):4832-42. doi: 10.1021/jo500698q. Epub 2014 May 15.
The power of hydrogen-bond donor catalysis has been harnessed to elicit and control carbene-like reactivity from nitrodiazoesters. Specifically, select ureas have been identified as effective catalysts for N-H insertion and multicomponent coupling reactions of nitrodiazoesters, anilines, and aromatic nucleophiles, thereby preparing a variety of α-aryl glycines in high yield. Experimental and computational studies designed to probe the plausible reaction pathways suggest that difluoroboronate ureas are particularly well-suited to catalyze reactions of nitrodiazoesters with a range of anilines through a polar reaction pathway. Urea-facilitated loss of nitrite followed by addition of a nucleophile conceivably generates the observed aryl glycine products.
氢键供体催化的能力已被用于引发和控制硝基亚胺二乙酯的卡宾样反应活性。具体而言，已确定某些脲是硝基亚胺二乙酯、苯胺和芳族亲核试剂的N-H插入和多组分偶联反应的有效催化剂，从而以高产率制备了多种α-芳基甘氨酸。旨在探究可能反应途径的实验和计算研究表明，二氟硼酸酯脲特别适合通过极性反应途径催化硝基亚胺二乙酯与一系列苯胺的反应。可以想象，脲促进亚硝酸盐的离去，随后亲核试剂的加成生成了观察到的芳基甘氨酸产物。
