文献类型：期刊文献

英文题名：Controllable Synthesis of Trifluoromethyl- or gem-Difluorovinyl-containing Analogues of Neonicotinoids by the Reaction of α-(Trifluoromethyl)styrenes with 2-Nitroimino-imidazolidine

作者：He, Jingjing[1];Sun, Zhudi[1];Deng, Yupian[1];Liu, Ying[1];Zheng, Pai[1];Cao, Song[1,2]

机构：[1]East China Univ Sci & Technol ECUST, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China;[2]Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

年份：2023

卷号：28

期号：8

外文期刊名：MOLECULES

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000980915400001)】；

语种：英文

外文关键词：alpha-(trifluoromethyl)styrenes; 2-nitroimino-imidazolidine; trifluoromethyl- or gem-difluorovinyl-containing analogues of neonicotinoids

摘要：A simple and straightforward addition or defluorination of alpha-(trifluoromethyl)styrenes with 2-nitroimino-imidazolidine (2a), 2-(nitromethylene)imidazolidine (2b), 2-cyanoimino-thiazolidine (2c), and (E)-1-methyl-2-nitroguanidine (2d), in a controlled manner, was developed. The hydroamination of ff-(trifluoromethyl)styrenes with 2a, 2b, 2c, and 2d was completed in the presence of DBN at room temperature within 0.5-6 h, affording structurally diverse beta-trifluoromethyl- beta-arylethyl analogues of neonicotinoids in moderate to good yields. The gamma, gamma-difluoro- beta-arylallyl analogues of neonicotinoids were also successfully synthesized via defluorination of alpha-(trifluoromethyl)styrenes, with 2a and 2c using NaH as base at an elevated temperature together with a prolonged reaction time of 12 h. The method features simple reaction setup, mild reaction conditions, broad substrate scope, high functional group compatibility, and easy scalability.