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Synthesis of Trifluoromethyl Ketones via Tandem Claisen Condensation and Retro-Claisen C-C Bond-Cleavage Reaction

Dongmei Yang, Yuhan Zhou*, Na Xue and Jingping Qu*

*State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian 116024, P.R. China, Email: zhouyhdl.cn, qujpdlut.edu.cn

D. Yang, Y. Zhou, N. Xue, J. Qu, J. Org. Chem., 2013, 78, 4171-4176.

DOI: 10.1021/jo400280p (free Supporting Information)


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Abstract

A tandem process of a Claisen condensation and a retro-Claisen C-C bond cleavage enables an efficient, operationally simple approach to trifluoromethyl ketones. Enolizable alkyl phenyl ketones readily react with ethyl trifuoroacetate under the promotion of NaH to afford trifluoromethyl ketones. This procedure can be extended to the preparation of perfluoroalkyl ketones in excellent yield.

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Key Words

Trifluoromethyl Ketones, Claisen Condensation


ID: J42-Y2013