Stevanović Dragana, Bugarinović Jovana, Pešić Marko, Todosijević Anka, Bogdanović Goran A, Damljanović Ivan
Faculty of Science, University of Kragujevac 34000 Kragujevac Serbia
Faculty of Agriculture, University of Niš 37000 Kruševac Serbia.
RSC Adv. 2021 Nov 10;11(57):36208-36214. doi: 10.1039/d1ra07619a. eCollection 2021 Nov 4.
A simple protocol has been developed for the chemoselective synthesis of ferrocene-containing Rauhut-Currier adducts from 1-ferrocenyl-2-nitroethene and vinyl ketones using 20 mol% of triphenylphosphine. Multifunctional ferrocene derivatives were obtained in moderate to high yields (51-92%) by the coupling between the α-position of vinyl ketones and the β-position of the nitroalkene. The study of the Rauhut-Currier reaction under the described conditions showed that the strong electron-donating group at the β-position of nitroalkenes plays a significant role in the reaction outcome due to prevention of polymerization and stabilization of the zwitterionic intermediate. Additionally, a preparative synthesis of 4-ferrocenyl-3-methylene-5-nitropentan-2-one was carried out and its synthetic transformations showed easy conversion to other useful building blocks.
已经开发出一种简单的方法，使用20 mol%的三苯基膦，从1-二茂铁基-2-硝基乙烯和乙烯基酮化学选择性合成含二茂铁的劳胡特-库里尔加合物。通过乙烯基酮的α-位与硝基烯烃的β-位之间的偶联，以中等至高收率（51-92%）获得了多功能二茂铁衍生物。在所描述的条件下对劳胡特-库里尔反应的研究表明，硝基烯烃β-位的强供电子基团由于防止聚合和稳定两性离子中间体，在反应结果中起重要作用。此外，还进行了4-二茂铁基-3-亚甲基-5-硝基戊-2-酮的制备合成，其合成转化显示易于转化为其他有用的结构单元。
