Synthesis of polysubstituted 5-trifluoromethyl isoxazoles via denitrogenative cyclization of vinyl azides with trifluoroacetic anhydride

Wei Wu; Qiaoling Chen; Yishi Tian; Yihui Xu; Yangjie Huang; Yi You; Zhiqiang Weng

doi:10.1039/D0QO00243G

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Synthesis of polysubstituted 5-trifluoromethyl isoxazoles via denitrogenative cyclization of vinyl azides with trifluoroacetic anhydride†

Wei Wu,^a Qiaoling Chen,‡^a Yishi Tian,‡^a Yihui Xu,‡^a Yangjie Huang,*^a Yi You*^a and Zhiqiang Weng

*^a

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* Corresponding authors

^a State Key Laboratory of Photocatalysis on Energy and Environment, and Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, China
E-mail: 373564427@qq.com, youyi@fzu.edu.cn, zweng@fzu.edu.cn
Tel: +86 591 22866234

Abstract

We describe a general method for the synthesis of 5-(trifluoromethyl)isoxazoles by denitrogenative cyclization of vinyl azides with trifluoroacetic anhydride in the presence of NEt₃. The scope of this protocol was further extended to the synthesis of perfluoroalkylated isoxazoles. This reaction allows facile synthesis of structurally diverse 5-(perfluoroalkyl)isoxazole derivatives with various vinyl azides.

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DOI: https://doi.org/10.1039/D0QO00243G
Article type: Research Article
Submitted: 24 Feb 2020
Accepted: 05 Jun 2020
First published: 08 Jun 2020

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Org. Chem. Front., 2020,7, 1878-1883

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Synthesis of polysubstituted 5-trifluoromethyl isoxazoles via denitrogenative cyclization of vinyl azides with trifluoroacetic anhydride

W. Wu, Q. Chen, Y. Tian, Y. Xu, Y. Huang, Y. You and Z. Weng, Org. Chem. Front., 2020, 7, 1878 DOI: 10.1039/D0QO00243G

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Organic Chemistry Frontiers

Synthesis of polysubstituted 5-trifluoromethyl isoxazoles via denitrogenative cyclization of vinyl azides with trifluoroacetic anhydride†

Abstract

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Synthesis of polysubstituted 5-trifluoromethyl isoxazoles via denitrogenative cyclization of vinyl azides with trifluoroacetic anhydride

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