Copper-Catalyzed Fluoroolefination of Silyl Enol Ethers and Ketones toward the Synthesis of β-Fluoroenones

Yanlin Li, Jing Liu, Shuang Zhao, Xuzhao Du, Minjie Guo*, Wentao Zhao, Xiangyang Tang and Guangwei Wang*

*Health and Science Platform and School of Science, Tianjin University, Tianjin 300072, P. R. China, Email: wanggwtju.edu.cn, gmj2016tju.edu.cn

Y. Li, J. Liu, S. Zhao, Y. Du, M. Guo, W. Zhao, X. Tang, G. Wang, Org. Lett., 2018, 20, 917-920.

DOI: 10.1021/acs.orglett.7b03700

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Abstract

A copper-amine catalyst system enables a general and facile synthetic method for β-fluoroenones from silyl enol ethers or ketones via tandem process of difluoroalkylation-hydrolysis-dehydrofluorination. This reaction offers high yields, excellent Z/E ratios, a low-cost catalyst, and a broad substrate scope.

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proposed mechanism

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Key Words

enones, α,β-unsatured esters, fluoroalkenes

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ID: J54-Y2018