Waetzig Shelli R, Tunge Jon A
Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
J Am Chem Soc. 2007 Dec 5;129(48):14860-1. doi: 10.1021/ja077070r. Epub 2007 Nov 8.
Allylic esters of nitrobenzene acetic acids undergo facile palladium-catalyzed decarboxylative coupling. Both mono- and dinitroarene substrates give high yields of the coupled products. Moreover, the rates of the reactions suggest that decarboxylation is rate-limiting and substrates that sterically disfavor attainment of the reactive conformation for decarboxylation are not viable. Finally, reduction of the product nitroarenes to the corresponding anilines provides access to a variety of heterocycles including quinolines and dihydroquinolones.
硝基苯乙酸的烯丙基酯可 facile 地进行钯催化的脱羧偶联反应。单硝基芳烃和二硝基芳烃底物均能以高产率得到偶联产物。此外，反应速率表明脱羧是限速步骤，在空间上不利于达到脱羧反应活性构象的底物是不可行的。最后，将产物硝基芳烃还原为相应的苯胺可用于合成多种杂环化合物，包括喹啉和二氢喹啉酮。
