Synthesis of Trifluoromethylated Indole/Benzimidazole-Fused Pyrrolidines or Piperidines via Visible-Light-Driven Radical Trifluoromethylation/Cyclization

doi:10.6023/cjoc202604033

Chinese Journal of Organic Chemistry

ARTICLE

可见光驱动的自由基三氟甲基化/环化反应合成三氟甲基化的吲哚/苯并咪唑稠合吡咯烷或哌啶衍生物

潘晓娜, 温欢, 王克虎, 王君姣, 黄丹凤^*, 胡雨来^*

西北师范大学化学化工学院兰州 730070

收稿日期:2026-04-23 修回日期:2026-06-02
基金资助:
国家自然科学基金(No. 22461038)资助项目.

Synthesis of Trifluoromethylated Indole/Benzimidazole-Fused Pyrrolidines or Piperidines via Visible-Light-Driven Radical Trifluoromethylation/Cyclization

Pan Xiaona, Wen Huan, Wang Ke-Hu, Wang Junjiao, Huang Danfeng^*, Hu Yulai^*

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received:2026-04-23 Revised:2026-06-02
Contact: ^*E-mail: huangdf@nwnu.edu.cn; huyl@nwnu.edu.cn.
Supported by:
National Natural Science Foundation of China (No. 22461038).

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Abstract

A visible-light-induced radical trifluoromethylation/cyclization reaction of N-isopentenyl/N-4-methyl-3-penten-1-yl-indoles or N-isopentenyl/ N-4-methyl-3-penten-1-yl-benzimidazoles is reported using with CF₃Br as cost-effective and readily available trifluoromethylating reagent. This method enables the efficient construction of trifluoromethyl-substituted indole/benzimidazole-fused pyrrolidine or piperidine derivatives under mild conditions. The protocol exhibits the advantages of high functional group compatibility, a broad substrate scope, and the use of visible light as a green energy source.

Key words: Radical Cascade Cyclization, Trifluoromethylation, Trifluoromethyl Bromide, Indole-fused Pyrrolidines, Indole-fused Piperidines

Cite this article

Pan Xiaona, Wen Huan, Wang Ke-Hu, Wang Junjiao, Huang Danfeng, Hu Yulai. Synthesis of Trifluoromethylated Indole/Benzimidazole-Fused Pyrrolidines or Piperidines via Visible-Light-Driven Radical Trifluoromethylation/Cyclization[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202604033.

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(马然松,邓周斌,王克虎,黄丹凤,胡雨来,吕肖波,有机化学,2022,43,353)

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可见光驱动的自由基三氟甲基化/环化反应合成三氟甲基化的吲哚/苯并咪唑稠合吡咯烷或哌啶衍生物

Synthesis of Trifluoromethylated Indole/Benzimidazole-Fused Pyrrolidines or Piperidines via Visible-Light-Driven Radical Trifluoromethylation/Cyclization

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