Trifluoromethyl Ketones from Enolizable Carboxylic Acids via Enediolate Trifluoroacetylation/Decarboxylation

…, Z Tan, H Lee, NK Yee, CH Senanayake

Index: Reeves, Jonathan T.; Song, Jinhua J.; Tan, Zhulin; Lee, Heewon; Yee, Nathan K.; Senanayake, Chris H. Journal of Organic Chemistry, 2008 , vol. 73, # 23 p. 9476 - 9478

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Citation Number: 15

Abstract

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 ...