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Synfacts 2009(3): 0315-0315
DOI: 10.1055/s-0028-1087709
DOI: 10.1055/s-0028-1087709
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Trifluoromethyl Ketones via Enediolate Trifluoroacetylation-Decarboxylation
J. T. Reeves*, J. J. Song, Z. Tan, H. Lee, N. K. Yee, C. H. Senanayake
Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
19. Februar 2009 (online)
Significance
Primary and secondary enolizable carboxylic acids and lithium carboxylates were successfully transformed into the corresponding trifluoromethylketones in a simple one-pot procedure via a) deprotonation to the enediolate with LDA, b) addition of F3CCO2Et, and c) decarboxylation through acidic quenching. This method could also be applied to the preparation of pentafluoroethyl and chlorodifluoromethyl ketones.