Insights into Deoxytrifluoromethylation/Aromatization to Access Highly Substituted Trifluoromethyl Arenes

A recently developed deoxyfluoroalkylation/aromatization strategy enables conversion of cyclohexan(en)ones to highly substituted trifluoromethyl arenes (Ar–CF3). In the prior communications, key mechanistic details and physicochemical considerations were not fully articulated; in particular, the physicochemical perturbations imparted by the CF3 group that disfavors the aromatization step. Additionally, several functional group and substrates did not perform well using the standard conditions, and reoptimization of the reactions was required to deliver synthetically useful yields of desired products. Herein, we present the reaction design along with mechanistic and practical insights behind the reactions that will help future chemists adapt this strategy to a broad range of substrates. Additionally, demonstration of the reaction on a muti gram scale, establishes its potential for large-scale applications.