Metal-free quinoline synthesis <i>via</i> Brønsted acid-promoted cyclization of ene-ynamides

We report a metal-free strategy for the efficient synthesis of polysubstituted quinolines <i>via</i> Brønsted acid-promoted cyclization of readily accessible ene-ynamides. Promoted by stoichiometric TfOH under mild conditions (30 °C), this method transforms simple, modular substrates into a wide range of quinoline derivatives in a single step, eliminating the need for precious-metal catalysts or prefunctionalized reagents. Its broad functional group tolerance and successful gram-scale operation underscore the method's practical utility and potential for broader application.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-12-30
DOI
https://doi.org/10.1039/d5ob01680k
Primary Topic
Catalytic Alkyne Reactions
Type
article
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article

Metal-free quinoline synthesis via Brønsted acid-promoted cyclization of ene-ynamides

Junbiao Chang, Xiaona Wang, Lisha Zhang, Yu Li et al.
Organic & Biomolecular Chemistry
Catalytic Alkyne Reactions
article

Metal-free quinoline synthesis via Brønsted acid-promoted cyclization of ene-ynamides

Junbiao Chang, Xiaona Wang, Lisha Zhang, Yu Li, Yijie Wang
article en

Abstract

We report a metal-free strategy for the efficient synthesis of polysubstituted quinolines <i>via</i> Brønsted acid-promoted cyclization of readily accessible ene-ynamides. Promoted by stoichiometric TfOH under mild conditions (30 °C), this method transforms simple, modular substrates into a wide range of quinoline derivatives in a single step, eliminating the need for precious-metal catalysts or prefunctionalized reagents. Its broad functional group tolerance and successful gram-scale operation underscore the method's practical utility and potential for broader application.

Organic & Biomolecular ChemistryVol. 24(4)
Zhengzhou University (CN)
Openalex Percentile: Top 33%
Catalytic Alkyne Reactions
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