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Trifluoromethyl Ketones from Enolizable Carboxylic Acids via Enediolate Trifluoroacetylation/Decarboxylation

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journal contribution
posted on 05.12.2008, 00:00 by Jonathan T. Reeves, Jinhua J. Song, Zhulin Tan, Heewon Lee, Nathan K. Yee, Chris H. Senanayake
Primary and secondary (enolizable) carboxylic acids were converted in a single step to trifluoromethyl ketones. Treatment of the acid with 2.2 equiv of LDA generated an enediolate that was trifluoroacetylated with EtO2CCF3. Quenching the reaction mixture with aqueous HCl resulted in rapid decarboxylation and provided the trifluoromethyl ketone product in good yield. The process may be performed at −20 °C with a slight reduction in yield. The reaction was extended to the preparation of pentafluoroethyl and chlorodifluoromethyl ketones.