Electrochemical Tri- and Difluoromethylation-Triggered Cyclization Accompanied by the Oxidative Cleavage of Indole Derivatives

Xin Yuan, Yu Sheng Cui, Xin Peng Zhang, Long Zhou Qin, Qi Sun, Xiu Duan, Lin Chen, Guigen Li, Jiang Kai Qiu, Kai Guo

Research output: Contribution to journalArticlepeer-review

Abstract

Considering their unique roles in organic synthesis, and pharmaceutical and agrochemical applications, the development of fluoroalkylation, cyclization, and indole oxidative cleavage are important topics. Herein, an unprecedented electrochemical tri- and difluoromethylation/cyclization/indole oxidative cleavage process occurring in an undivided cell is presented. The protocol employs a readily prepared Langlois reagent as the fluoroalkyl source, affording a series of tri- or difluoromethylated 2-(2-acetylphenyl)isoquinoline-1,3-diones in good yields with excellent stereoselectivity. It is worth noting that this new methodology merges the fluoroalkylation/cyclization of N-substituted acrylamide alkenes with the oxidative cleavage of an indole C(2)=C(3) bond under external oxidant-free conditions.

Original languageEnglish
Pages (from-to)6522-6528
Number of pages7
JournalChemistry - A European Journal
Volume27
Issue number21
DOIs
StatePublished - Apr 12 2021

Keywords

  • cyclization
  • electrochemistry
  • fluoroalkylation
  • indole oxidative cleavage
  • tri- and difluoromethylation

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