The selective synthesis of fluoroarene compounds has become a subject of growing interest due to the prominent role such species play in many modern pharmaceuticals, agrochemicals and other industrially important products. An attractive route for the selective substitution of fluoroarenes is based on the functionalization of activated aromatic C–F bonds derived from readily available perfluoroarenes. The presentation covers the synthesis and reactivity of NHC-stabilized nickel complexes, which transfer [Ni(R2Im)2] (R2Im = 1,3-di(organyl)imidazole-2-ylidene) in stoichiometric and catalytic reactions under mild conditions, and their use in the functionalization to polyfluorinated arenes. Current developments of methodologies to generate and use suitable fluorinated organic precursors are presented. These strategies employ, for example, (i) C-F functionalization of polyfluoroaromatics or (ii) use of the polyfluoroaromatics or fluoroaryl boronic ester in subsequent Suzuki-Miyaura coupling reactions.

NHC-nickel-catalyzed derivatization of polyfluoroarenes via nickel-mediated C-F bond cleavage

255th National Meeting (2018)

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