Direct Access to α-Trifluoromethyl Enones via Efficient Copper-Catalyzed Trifluoromethylation of Meyer-Schuster Rearrangement

Ya-Ping Xiong, Ming-Yue Wu, Xiang-Yu Zhang, Can-Liang Ma, Lin Huang, Li-Jiao Zhao, Bin Tan* and Xin-Yuan Liu*

*Department of Chemistry South University of Science and Technology of China, Shenzhen, 518055, P. R. China, Email: tanbsustc.edu.cn., liuxy3sustc.edu.cn

Y.-P. Xiong, M.-Y. Wu, X.-Y. Zhang, C.-L. Ma, L. Huang, L.-J. Zhao, B. Tan, X.-Y. Liu, Org. Lett., 2014, 16, 1000-1003.

DOI: 10.1021/ol403741m

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Abstract

A novel domino copper-catalyzed trifluoromethylated Meyer-Schuster rearrangement reaction with Togni's reagent provides α-trifluormethyl enones with moderate to good yields. Furthermore, these α-CF₃ enones can be transformed toward interesting trifluoromethyl-substituted heterocycles in a one-pot reaction.

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Key Words

trifluoromethylation, hydration

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ID: J54-Y2014