Synthesis of Perfluoro-<i>tert</i>-butyl Triazoles via Decarboxylative CuAAC of (Perfluoro-<i>tert</i>-butyl)propiolic Acid with Azides

A copper-catalyzed decarboxylative cycloaddition of (perfluoro-<i>tert</i>-butyl)propiolic acid (PFtPA) with azides under mild conditions was developed, enabling the facile synthesis of perfluoro-<i>tert</i>-butyl (PFtB) triazoles. The strong electron-withdrawing nature of the PFtB group facilitates efficient decarboxylative cycloaddition at 30 °C using catalytic copper acetate, avoiding the requirement of traditional harsh conditions. This method provides high yields of products and is compatible with a wide range of azides (including bioactive molecules). This protocol serves as a robust synthetic tool for late-stage fluorination of bioactive compounds, as well as for the development of highly sensitive <sup>19</sup>F NMR probes.

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Publication Details

Journal
Organic Letters
Published
2025-06-16
DOI
https://doi.org/10.1021/acs.orglett.5c02101
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthesis of Perfluoro-tert-butyl Triazoles via Decarboxylative CuAAC of (Perfluoro-tert-butyl)propiolic Acid with Azides

Mingyou Hu, Jinbo Hu, Yao Chen, Haixia Song et al.
Organic Letters
Fluorine in Organic Chemistry
article

Synthesis of Perfluoro-tert-butyl Triazoles via Decarboxylative CuAAC of (Perfluoro-tert-butyl)propiolic Acid with Azides

Mingyou Hu, Jinbo Hu, Yao Chen, Haixia Song, Zhiqiang Wei, Chuanfa Ni
article en

Abstract

A copper-catalyzed decarboxylative cycloaddition of (perfluoro-<i>tert</i>-butyl)propiolic acid (PFtPA) with azides under mild conditions was developed, enabling the facile synthesis of perfluoro-<i>tert</i>-butyl (PFtB) triazoles. The strong electron-withdrawing nature of the PFtB group facilitates efficient decarboxylative cycloaddition at 30 °C using catalytic copper acetate, avoiding the requirement of traditional harsh conditions. This method provides high yields of products and is compatible with a wide range of azides (including bioactive molecules). This protocol serves as a robust synthetic tool for late-stage fluorination of bioactive compounds, as well as for the development of highly sensitive <sup>19</sup>F NMR probes.

Organic LettersVol. 27(25)
ShanghaiTech University (CN), Shanghai Institute of Organic Chemistry (CN), University of Chinese Academy of Sciences (CN)
National Natural Science Foundation of China, Chinese Academy of Sciences
Clean water and sanitation
Openalex Percentile: Top 90%
Fluorine in Organic Chemistry
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