Hydrodefluorination is a process that converts a C-F bond to a C-H bond, which is significant in creating novel therapeutic agents. By keeping this in mind, we sought to showcase the synthetic potential of imine-based N-difluoromethylated products using the hydrodefluorination approach. In this vein, we mixed 3a, NaBH4, and Al2O3 (all are solid reagents) and grinded with hand in a Mortar-pestle by slowly adding 30 drops of methanol (3 drops per minute). These conditions led to a valuable 3D shape N-methylated motif 21 in 47% isolated yield (Figure ), and this result underscores that our proposed synthetic strategy provides versatile access to high Fsp 3 -enriched scaffolds, which holds the promise of drug discovery in medicinal chemistry purposes. It should be noted that rapid synthesis of compound 21 with high Fsp 3 is difficult to access using conventional strategies. To gain insight into how the N-difluoromethylation reaction works, we conducted a few control experiments. Initially, we executed a deuterium labelling experiment with 1a using D2O (10 equiv.) under standard conditions. This experiment resulted in an 86% isolated yield of the desired deuterated product (d-3a) with 74% deuterium incorporation (Figure ). Next, we treated d-3a with H2O (10 equiv.) under the same conditions in the absence of 2e, and the result showed that there was no exchange of H-D; and d-3a was recovered with 79% isolated yield (Figure ), showcasing the stability of d-3a. Further, to identify the source of the H atom in the CF2-H unit of 3a, we carried out the reaction of d-1a (34%-D incorporation; for the preparation of d-1a, see ESI, Figure ) with 2e under standard conditions, but no deuterium incorporation was observed, and 3a was isolated with 89% yield (0%-D incorporation) (Figure ). This finding clearly validates that the hydrogen atom of the CF2-H unit in 3a is not a part of the N-H component of 1a. This implies that BrCF2CO2H could be a source of the H atom in the CF2H unit of 3a, which is corroborated by the literature. To know the reaction intermediate, we first treated 1a with 2e under standard conditions without adding K2CO3. The analysis of the crude reaction mixture by HRMS revealed the formation of intermediate 3a ′ , while the desired product 3a was not detected. Later, the addition of K2CO3 (2.5 equiv.) in the same reaction mixture resulted in the formation of 3a, evidencing the requirement of K2CO3 for transforming 3a ′ to 3a.