Nucleophilic trifluoromethylation of azinium salts with Zn(CF3)2·bpy

(Trifluoromethyl)zinc complexes have been widely used in metal-mediated trifluoromethylation reactions. However, direct nucleophilic addition with a (trifluoromethyl)zinc complex is rare. In this article, we describe an unprecedented trifluoromethylation of azinium salts using Zn(CF3)2·bpy as CF3 source, giving 1-(4-methoxybenzyl)-2-(trifluoromethyl)-1,2-dihydroquinolines as products. The latter species were further transformed to 2-trifluoromethylquinolines under oxidative conditions. This work also shows that ligands play an important role in tuning the reactivity of (trifluoromethyl)zinc complexes.