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Synthesis of Perfluoro-tert-butyl Triazoles via Decarboxylative CuAAC of (Perfluoro-tert-butyl)propiolic Acid with
Yao Chen1,2, Zhiqiang Wei1,2, Haixia Song1
1State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Abstract:
A copper-catalyzed decarboxylative cycloaddition of (perfluoro-tert-butyl)propiolic acid (PFtPA) with azides under mild conditions was developed, enabling the facile synthesis of perfluoro-tert-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 19F NMR probes.
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