Electrochemical Tandem Cyclization of <i>N</i> ‐(But‐3‐en‐1‐yl)Anilines to Access Trifluoromethylated Tetrahydroquinoline Derivatives

A novel electrochemical cascade strategy enables dual CC bond formation through trifluoromethylation and C(sp 2 )‐H functionalization of N ‐(but‐3‐en‐1‐yl)anilines derivatives. This protocol efficiently constructs structurally diverse trifluoromethylated tetrahydroquinoline derivatives in moderate to good yields. It operates under mild reaction conditions, uses readily available substrates, proceeds without metal catalysts, and achieves the construction of two CC bonds in a single step. Detailed mechanistic studies demonstrate that a sequential single‐electron transfer (SET) process triggers the radical cascade reaction.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-10-08
DOI
https://doi.org/10.1002/ejoc.202500634
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Electrochemical Tandem Cyclization of N ‐(But‐3‐en‐1‐yl)Anilines to Access Trifluoromethylated Tetrahydroquinoline Derivatives

Xue Yang, Yuanyuan Xie, Changjun Zhang, Hao Zhang et al.
European Journal of Organic Chemistry
Fluorine in Organic Chemistry
article

Electrochemical Tandem Cyclization of N ‐(But‐3‐en‐1‐yl)Anilines to Access Trifluoromethylated Tetrahydroquinoline Derivatives

Xue Yang, Yuanyuan Xie, Changjun Zhang, Hao Zhang, Yuxin Ding, Weike Su
article en

Abstract

A novel electrochemical cascade strategy enables dual CC bond formation through trifluoromethylation and C(sp 2 )‐H functionalization of N ‐(but‐3‐en‐1‐yl)anilines derivatives. This protocol efficiently constructs structurally diverse trifluoromethylated tetrahydroquinoline derivatives in moderate to good yields. It operates under mild reaction conditions, uses readily available substrates, proceeds without metal catalysts, and achieves the construction of two CC bonds in a single step. Detailed mechanistic studies demonstrate that a sequential single‐electron transfer (SET) process triggers the radical cascade reaction.

European Journal of Organic ChemistryVol. 28(40)
Ministry of Education (KR), State Key Laboratory of Chemical Engineering (CN), Zhejiang University of Technology (CN)
Openalex Percentile: Top 78%
Fluorine in Organic Chemistry
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Electrochemical Tandem Cyclization of <i>N</i> ‐(But‐3‐en‐1‐yl)Anilines to Access Trifluoromethylated Tetrahydroquinoline Derivatives — Xue Yang, Yuanyuan Xie, et al. · European Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS