American Chemical Society
jo400280p_si_001.pdf (3.64 MB)

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

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journal contribution
posted on 2013-04-19, 00:00 authored by Dongmei Yang, Yuhan Zhou, Na Xue, Jingping Qu
A highly efficient, operationally simple approach to trifluoromethyl ketones has been developed that builds on the use of a tandem process involving Claisen condensation and retro-Claisen C–C bond cleavage reaction. Enolizable alkyl phenyl ketones were found to react readily with ethyl trifuoroacetate under the promotion of NaH to afford trifluoroacetic ester/ketone exchange products, trifluoromethyl ketones, which were quite different from the general Claisen condensation products, β-diketones. This procedure uses readily available starting materials and can be extended to the preparation of perfluoroalkyl ketones in excellent yield.