Halotrifluoromethylation of 1,3-Enynes: Access to Tetrasubstituted Allenes

Jinfeng Huang, Yimin Jia, Xiangyu Li, Jianli Duan, Zhong-Xing Jiang and Zhigang Yang*

*Hubei Province Engineering and Technology Research Center for Fluorinated Pharmaceuticals, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, China, Email: zgyangwhu.edu.cn

J. Huang, Y. Jia, X. Li, J. Duan, Z.-X. Jiang, Z. Yang, Org. Lett., 2021, 23, 2314-2319.

DOI: 10.1021/acs.orglett.1c00449

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Abstract

A practical, convenient, and highly regioselective copper-catalyzed 1,4-chlorotrifluoromethylation of 1,3-enynes affords chloro- and CF₃-containing tetrasubstituted allene derivatives with very good yield. A 1,4-bromotrifluoromethylation is also reported.

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proposed mechanism

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Key Words

allenes, trifluoromethylation, chlorination, multicomponent reactions

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ID: J54-Y2021