文献类型：期刊文献

英文题名：Cycloaddition of trifluoromethyl ketimines with 2-alkenyl azaarenes through selective C-F bond cleavage of CF3

作者：Fu, Yiwei[1]; Qin, Cong[1]; Zhang, Zhiqiang[2]; Shi, Haoyu[1]; Zhao, Jianbo[1]; Gong, Xueqing[2]; Shi, Lei[3]; Li, Hao[1]

机构：[1] State Key Laboratory of Bioreactor Engineering, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China; [2] Key Laboratory for Advanced Materials, Joint International Research Laboratory for Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Centre for Computational Chemistry, Research Institute of Industrial Catalysis, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China; [3] Huabao Flavours and Fragrances Co. Ltd., 1299 Yecheng Road, Shanghai, 201822, China

年份：2021

卷号：8

期号：16

起止页码：4426

外文期刊名：Organic Chemistry Frontiers

收录：EI(收录号：20213410799530)

语种：英文

外文关键词：Chemical bonds

摘要：We have developed a new [4 + 2] cycloaddition of trifluoromethyl ketimines with 2-alkenyl azaarenes through selective C-F bond cleavage of CF3. The reactions are promoted by 2,2,6,6-tetramethylpiperidine (TMP) under mild conditions to give cis-tetrahydropyridine products in moderate yields. Density functional theory (DFT) calculations reveal that the in situ formed (E)-N-(2,2-difluoro-1-phenylvinyl)-1-phenylmethanimine is the key intermediate for the formation of cis-tetrahydropyridine products which have the lowest energy among the four possible products. This journal is ? the Partner Organisations.