Pd-catalyzed decarboxylative coupling of zinc polyfluorobenzoate with aryl imidazolylsulfonate for polyfluorinated biaryl synthesis.

Abstract

We report here an efficient decarboxylative cross-coupling of zinc polyfluorobenzoates with aryl imidazolylsulfonates under palladium catalysis, which proceeded effectively via C-O bond cleavage to afford the corresponding valuable polyfluorinated biaryls in moderate to good yields, exhibiting both reasonable substrate scope and broad functional group tolerance. In addition, late-stage functionalization of bioactive molecules and an amino acid-derived compound and scaled-up synthesis could be accomplished as well. Further exploration revealed that zinc polyfluorobenzoates are more vibrant than their potassium, sodium, and magnesium counterparts as a polyfluoroarylating reagent.