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.