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

Kaiqiang Zhuang, Yusheng Cui, Xin Yuan, Longzhou Qin, Qi Sun, Xiu Duan, Lin Chen, Xinpeng Zhang, Jiangkai Qiu, Kai Guo

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

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 CF3-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%).

Original languageEnglish
Pages (from-to)11729-11736
Number of pages8
JournalACS Sustainable Chemistry and Engineering
Volume8
Issue number31
DOIs
StatePublished - 10 Aug 2020

Keywords

  • 1,7-enynes
  • continuous-flow
  • cyclization
  • photoredox-catalyzed
  • trifluoromethylation

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