An expansive array of medicines, agrochemicals, and materials contain fluorine due to the unique chemical properties that the element confers on organic molecules. One of the chief obstacles to the discovery and production of these compounds is the availability of synthetic methods for carbon�fluorine (C�F) bond formation. The most abundant and inexpensive fluorine sources, nucleophilic fluoride salts, typically suffer from low solubility, high hygroscopicity, and strong Br�nsted basicity, rendering them recalcitrant reagents for chemical synthesis. Nevertheless, our laboratory has recently identified strategies that achieve mild and efficient nucleophilic fluorination using transition metal catalysis. This lecture will describe some of our recent progress in methodology development. Mechanistic studies will be discussed that contribute a better understanding of the properties and reactivity of transition metal fluorides. Furthermore, this lecture will cover application of our methods to the preparation of small-molecule tracers containing the radionuclide 18F for positron emission tomography (PET).

Award Address  (Arthur C. Cope Early Career Scholars Award sponsored by the Arthur C. Cope Fund). New reagents and strategies for catalytic nucleophilic fluorination

248th National Meeting (2014)

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