Visible-Light-Induced Trifluoromethylation/Cyclization of 1,7-Enynes in Continuous Flow

被引:19
|
作者
Zhuang, Kaiqiang [1 ]
Cui, Yusheng [1 ]
Yuan, Xin [1 ]
Qin, Longzhou [1 ]
Sun, Qi [1 ]
Duan, Xiu [1 ]
Chen, Lin [1 ]
Zhang, Xinpeng [1 ]
Qiu, Jiangkai [1 ]
Guo, Kai [1 ]
机构
[1] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, Nanjing 211816, Peoples R China
来源
基金
中国国家自然科学基金;
关键词
photoredox-catalyzed; trifluoromethylation; cyclization; 1,7-enynes; continuous-flow; CATALYZED CASCADE CYCLIZATION; OXIDATIVE TRIFLUOROMETHYLATION; PHOTOREDOX CATALYSIS; FACILE SYNTHESIS; FLUORINE; PERFLUOROALKYLATION; FUNCTIONALIZATION; HETEROARENES; N-ENYNES; ACCESS;
D O I
10.1021/acssuschemeng.0c03745
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the present study, we describe the successful development of a photoredox-catalyzed trifluoromethylation/cyclization of 1,7-enynes in a continuous-flow regime for the generation of several CF 3 -containing heterocyclic scaffolds. When using this protocol, a readily prepared Ph2SCF3OTf reagent was employed as the trifluoromethylation reagent, and various benzo[j]phenanthridines and indeno[1,2-c]quinolines were obtained in good to moderate yields. This transformation featured mild reaction conditions, a broad substrate scope, and ease of scale-up. Moreover, the continuous-flow processing in a photomicroreactor accelerated the reaction (5 min reaction time) and increased the product yields (up to 89%).
引用
收藏
页码:11729 / 11736
页数:8
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