Catalytic C-H/C-F Coupling of Azoles and Acyl Fluorides.

A method for the palladium/copper-catalyzed direct acylation of azoles with acyl fluorides is described. This study reports the first examples of acyl fluorides being used as acylation reagents in transition-metal-catalyzed aromatic C-H bond functionalization reactions. Depending on the reaction temperature, decarbonylative coupling may also occur. Mechanistic studies suggest that the cleavage of the aromatic C-H bond, promoted by a copper-phosphine species, is not the rate-limiting step of this acylation.