Palladium-Catalyzed Decarboxylative Cross-Couplings of Zinc Polyfluorobenzoates with Aryl 2-Pyridyl Esters for Accessing Polyfluorinated Aryl Ketones

An efficient decarboxylative cross-coupling of zinc polyfluorobenzoate with aryl 2-pyridyl ester under palladium catalysis, which enabled the convenient access to valuable polyfluorinated aryl ketones, was developed. The cross-coupling reactions proceeded effectively to give an array of polyfluorinated aryl ketones in moderate to excellent yields with a reasonable substrate scope and broad functional group tolerance. In addition, a one-pot reaction with the use of in situ formed zinc polyfluorobenzoate commencing from polyfluorobenzoic acid and Zn(OH)₂ could be accomplished as well in a step-economical fashion. Moreover, the coupling protocol could also be successfully subjected to scale-up synthesis and readily applied in the late-stage functionalization of biologically active complex molecules.