10.1021/jo400859s
The study presents a novel synthetic method for the production of 2-aryl-3-trifluoromethylquinolines, which are compounds of interest in pharmaceutical, agrochemical, and high-performance material sectors due to their significant roles. The researchers utilized a Hiyama cross-coupling reaction involving (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane and 2-iodoaniline, facilitated by copper(II) fluoride and 2,2′-bipyridyl as a fluoride source and ligand, respectively. This reaction yielded (E)-2-(3,3,3-trifluoroprop-1-enyl)aniline without the need for amino group protection. Subsequently, an oxidative cyclization reaction with aryl aldehydes in the presence of a copper(I) salt catalyst, specifically [Cu(OTf)]2·C6H6, led to the formation of the target quinolines. The study's purpose was to develop an efficient synthetic protocol to access 3-trifluoromethylquinolines, which are challenging to synthesize using conventional methods, and to expand the library of such compounds for potential therapeutic applications.