Copper-catalyzed aminotrifluoromethylation of unactivated alkenes with (TMS)CF3: Construction of trifluoromethylated azaheterocycles

Article abstract of DOI:10.1021/jo5012619

The first example of a copper(I)-catalyzed intramolecular aminotrifluoromethylation of unactivated alkenes using (TMS)CF₃ (trimethyl(trifluoromethyl)silane) as the CF₃ source is described. A broad range of electronically and structurally varied substrates undergo convenient and step-economical transformations for the concurrent construction of a five- or six-membered ring and a C-CF₃ bond toward different types of trifluoromethyl azaheterocycles. The methodology not only circumvents use of expensive electrophilic CF₃ reagents or the photoredox strategy but also expands the scope to substrates that are difficult to access by the existing methods. Mechanistic studies are conducted, and a plausible mechanism is proposed.