Mechanochemical Electrophilic Fluorination of Liquid Beta-Ketoesters

Analysis of an improved substrate scope for the mechanochemical electrophilic fluorination of dicarbonyls is reported. The applicable substrates have now been broadened to include liquid b-ketoesters. Key to this capability is the inclusion of a grinding auxiliary (NaCl) to improve mass transfer and prevent pasting or gumming of the reaction mixture. Notably, the use of a small amount of acetonitrile is ciritical to increasing the rate of reaction, ensuring complete consumption of starting materials during the short reaction times as well as improving the selectivity for the monofluorinated product in the mill. The data here contains a selection of 1H, 13C, 19F NMR data, as well as IR, MS and any relevant chromatography information. Some files may be processed in advance and deposited and some may require access to typical processing tools for data of this type.