Journal of the American Chemical Society 2006-07-12

Catalytic intermolecular direct arylation of perfluorobenzenes.

Marc Lafrance, Christopher N Rowley, Tom K Woo, Keith Fagnou

Index: J. Am. Chem. Soc. 128 , 8754, (2006)

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Abstract

Penta-, tetra-, tri-, and difluorobenzenes undergo direct arylation with a wide range of arylhalides in high yield. Inverse reactivity is observed compared to the common electrophilic aromatic substitution pathway since electron-deficient, C-H acidic arenes react preferentially. Computational studies indicate that C-H bond cleavage occurs via a concerted carbon-palladium and carbon-hydrogen bond cleaving event involving a carbonate or a bromide ligand. The reactions are rapid, require only a slight excess of the perfluoroarene reagent, and utilize commercially available, air-stable catalyst precursors.