Cu-Catalyzed Synthesis of Fluoroalkylated Isoxazoles from Commercially Available Amines and Alkynes

Xiao-Wei Zhang, Wen-Li Hu, Suo Chen and Xiang-Guo Hu*

*National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang, 330022, China, Email: huxianggiccas.ac.cn

X.-W. Zhang, W.-L. Hu, S. Chen, X.-G. Hu, Org. Lett., 2018, 20, 860-863.

DOI: 10.1021/acs.orglett.7b04028

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Abstract

A one-pot protocol for the construction of fluoroalkylated isoxazoles directly from commercially available amines and alkynes is regioselective, scalable, operationally simple, mild, and tolerant of a broad range of functional groups. Preliminary mechanistic investigations reveal that the transformation involves an unprecedented Cu-catalyzed cascade sequence involving R_fCHN₂.

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proposed mechanism

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Key Words

Isoxazoles, tert-Butyl nitrite, multicomponent reactions

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ID: J54-Y2018