文献类型：期刊文献

英文题名：[4+2] Cycloaddition of trifluoromethyl ketimines with 2-alkenyl azaarenes through selective C-F bond cleavage of CF3

作者：Fu, Yiwei[1,2];Qin, Cong[1,2];Zhang, Zhiqiang[3,4,5];Shi, Haoyu[1,2];Zhao, Jianbo[1,2];Gong, Xueqing[3,4,5];Shi, Lei[6];Li, Hao[1,2]

机构：[1]East China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China;[4]East China Univ Sci & Technol, Sch Chem & Mol Engn, Joint Int Res Lab Precis Chem & Mol Engn, Feringa Nobel Prize Scientist Joint Res Ctr,Ctr C, 130 Meilong Rd, Shanghai 200237, Peoples R China;[5]East China Univ Sci & Technol, Sch Chem & Mol Engn, Res Inst Ind Catalysis, 130 Meilong Rd, Shanghai 200237, Peoples R China;[6]Huabao Flavours & Fragrances Co Ltd, 1299 Yecheng Rd, Shanghai 201822, Peoples R 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：;WOS:【SCI-EXPANDED(收录号:WOS:000661587300001)，CCR-EXPANDED(收录号:WOS:000661587300001)】；

基金：This work was supported by the program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning (GZ2017007) and the China 111 Project (Grant B07023).

语种：英文

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.