Organofluorine compounds have emerged as valuable synthetic targets for many important applications, including pharmaceuticals, agrochemicals, and radiotracers. The reactivity and molecular conformation of these fluorinated organic molecules are significantly impacted by the polarity of the carbon-fluorine bond. Despite the low cost and accessibility of fluoride sources, however, methods to construct carbon-fluorine bonds using nucleophilic fluoride remain limited. This presentation will describe the synthesis of alpha-fluorocarbonyl compounds using potassium fluoride as a nucleophilic fluoride source. Access to this medicinally-relevant motif is achieved using transition metal catalysis to effect the mild, efficient fluorination of diazo compounds. In addition, the application of this strategy to radiofluorination for positron emission tomography will be presented.

Copper-catalyzed H-F insertions

251st National Meeting (2016)

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