Fluorine-containing aromatic compounds are widespread in medicinal chemistry and material sciences, due to their unique stability, reactivity, and biological properties. Compounds containing a fluorinated aromatic ring or a trifluoromethyl group are particularly valuable, but methods to prepare these compounds under mild conditions with broad scope have been challenging to develop. During the past several years, we have sought to exploit our expertise in the synthesis of copper complexes that are intermediates in cross coupling, our expertise in palladium-catalyzed coupling reactions, and our methods to conduct C-H bond functionalization of arenes to develop methods for the conversion of aromatic compounds to aryl fluorides and aryl fluoroalkyl compounds. This lecture will describe our results on cross coupling related to the incorporation of fluorine and fluoroalkyl groups into aromatic molecules, along with a discussion of the fundamental organometallic chemistry addressed by this methods development and the mechanisms of these new classes of reactions.

Metal-mediated and metal-catalyzed coupling for incorporation of fluorine into aromatic molecules

249th National Meeting (2015)

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