Trifluoromethyl Ketones from Enolizable Carboxylic Acids via Enediolate Trifluoroacetylation/Decarboxylation
Jonathan T. Reeves*, Jinhua J. Song, Zhulin Tan, Heewon Lee, Nathan K. Yee and Chris H. Senanayake
*Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, Email: jonathan.reevesboehringer-ingelheim.com
J. T. Reeves, J. J. Song, Z. Tan, H. Lee, N. K Yee, C. H. Senanayake, J. Org. Chem., 2008, 73, 9476-9478.
DOI: 10.1021/jo801737c (free Supporting Information)
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Enolizable carboxylic acids were converted in a single step to trifluoromethyl ketones. Treatment of the acid with 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.
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