Mechanochemical decarbonylative transformation of the amide group into OCF3 and CF3 functionalities under ruthenium catalysis

Abstract

A novel strategy has been introduced for the selective activation of the N–C(O) moiety in primary aromatic amides through the utilization of pyrylium tetrafluoroborate under mechanochemical conditions, where the amide group undergoes subsequent activation and is selectively substituted with the CF₃ or OCF₃ functionality. The scope of the present protocol includes selective transformation of diversely substituted aromatic amides into the respective trifluoromethyl and trifluoromethoxy arenes via mechanochemically induced deaminative functionalization under the synergy of a piezoelectric material barium titanate (BaTiO₃) and ruthenium-catalysis. The presented mechanochemical approach unlocks new chemical spaces in the pharmaceutical industry with an emphasis on PASE (pot, atom, and step economy) synthesis.