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

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Indexed by:期刊论文

Date of Publication:2013-04-19

Journal:JOURNAL OF ORGANIC CHEMISTRY

Included Journals:SCIE、EI、PubMed、Scopus

Volume:78

Issue:8

Page Number:4171-4176

ISSN No.:0022-3263

Abstract: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, beta-diketones. This procedure uses readily available starting materials and can be extended to the preparation of perfluoroalkyl ketones in excellent yield.

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