Subsequent deprotonation facilitated the regeneration of the aromatic system, ultimately yielding the desired trifluoromethylated product 3. The theoretical viability of this reaction pathway is supported by DFT calculations which also suggest a possible mechanism for alternative regioselective product formation involving the preferential insertion of the incoming radical in para position. This analysis revealed that the preferential position (the para-position) for aromatic functionalization, is less hindered and complementarity to the approaching radical species.