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.
Authors
- Mingyou Hu (ORCID: https://orcid.org/0000-0002-7892-7338)
- Jinbo Hu (ORCID: https://orcid.org/0000-0003-3537-0207)
- Yao Chen (ORCID: https://orcid.org/0000-0003-0147-8156)
- Haixia Song
- Zhiqiang Wei (ORCID: https://orcid.org/0000-0002-3304-1269)
- Chuanfa Ni (ORCID: https://orcid.org/0000-0002-2296-8835)
Institutions
- ShanghaiTech University (CN)
- Shanghai Institute of Organic Chemistry (CN)
- University of Chinese Academy of Sciences (CN)
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
Funders
- National Natural Science Foundation of China
- Chinese Academy of Sciences