posted on 2013-04-19, 00:00authored byDongmei 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.