Alkaline Mineralization of Aryl Trifluoromethyl Groups Near Benzylic N -Heterocycles

We report the defluorination of trifluoromethyl arenes bearing an ortho N-heterocycle upon reaction with KOtBu in THF at ambient temperature; the trifluoromethyl group converts to the corresponding t-Bu ester. We demonstrated 14 examples of defluorination with up to 85% yield. Our findings should inform synthetic route design for targets containing these functional groups. Moreover, our findings suggest that similar compounds will defluorinate into inorganic fluoride upon treatment with a base.