Regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles via photocycloaddition of sydnone with CF3CN

Bo Lin; Yunfei Yao; Yangjie Huang; Qi Lin; Zhiqiang Weng

doi:10.1039/D2CC03928A

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Regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles via photocycloaddition of sydnone with CF₃CN†

Bo Lin,‡^ab Yunfei Yao,‡^b Yangjie Huang,*^a Qi Lin^a and Zhiqiang Weng

*^ab

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* Corresponding authors

^a Fujian Engineering Research Center of New Chinese lacquer Material, College of Materials and Chemical Engineering, Minjiang University, Fuzhou, China
E-mail: zweng@mju.edu.cn

^b Key Laboratory of Molecule Synthesis and Function Discovery, and Fujian Provincial Key Laboratory of Electrochemical Energy Storage Materials, College of Chemistry, Fuzhou University, Fuzhou, China

Abstract

A general and regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles has been achieved through photocycloaddition of sydnone with trifluoroacetonitrile. This method employed trifluoroacetaldehyde O-(aryl)oxime as the CF₃CN precursor and tolerated various functional groups to furnish 3-trifluoromethyl 1,2,4-triazole products in moderate to good yields. Mechanistic experiments revealed an energy transfer from photocatalyst 4-CzIPN to the sydnone substrates.

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Article information

DOI: https://doi.org/10.1039/D2CC03928A
Article type: Communication
Submitted: 14 Jul 2022
Accepted: 04 Oct 2022
First published: 10 Oct 2022

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Chem. Commun., 2022,58, 12224-12227

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Regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles via photocycloaddition of sydnone with CF₃CN

B. Lin, Y. Yao, Y. Huang, Q. Lin and Z. Weng, Chem. Commun., 2022, 58, 12224 DOI: 10.1039/D2CC03928A

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Chemical Communications