Download PDF
Synfacts 2009(3): 0315-0315  
DOI: 10.1055/s-0028-1087709
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Trifluoromethyl Ketones via Enediolate Trifluoroacetylation-Decarboxylation

Contributor(s): Paul Knochel, Tobias Thaler
J. T. Reeves*, J. J. Song, Z. Tan, H. Lee, N. K. Yee, C. H. Senanayake
Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, USA
Further Information

Publication History

Publication Date:
19 February 2009 (online)

    Permissions and Reprints

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.