Based on the results obtained from our control experiments and literature precedents, we proposed a probable reaction mechanism (Figure ). Although, 2e is known to generate a CF2 carbene precursor in a basic medium, but surprisingly the formation of intermediate 3a ′ without a base directed the first step of the reaction to be a simple nucleophilic substitution reaction between the starting material (12) and 2e. The more nucleophilicity of the N-atom of N-heteroarene (12) and a rapid release of CO2 gas via decarboxylation resulted formation of intermediate 13. It is presumed that the formation of intermediate 13 renders the N-H bond dissociation energy via increasing the acidity of the H-atom attached to the N-H bond, which could be probably due to the electron-withdrawing nature of the N-heteroarene (intermediate 13). Finally, K2CO3 abstracts the acidic proton from the N-H bond and generates another intermediate 14, which further undergoes π electron transfer to deliver the highly stabilized N-difluoromethylated product featuring an imine (15) functional group (Figure ). Importantly, our methodology was found to be highly efficient and suitable for N-aromatic substituted heteroarene-4-amines. For instance, when N-methylpyridin-4-amine (16a) and chloroquine (16b) were applied to the difluoromethylation under standard conditions, only a trace amount of corresponding products 17a, and 17b, respectively, was detected (analysed by F NMR). Whereas amodiaquine (1ak) was successfully transformed into imine-based N-difluoromethylated product 3ak. This protocol has some limitations with 4-methyl pyridine systems (18a) which may be due to less acidity of the H-atom of C(sp 3 )-H bond.