In conclusion, this study demonstrates that the remarkable reactivity at the gas-liquid interface extends beyond aqueous systems and is applicable to organic systems. Utilizing chemoselective double C-N cleavage, eight imidazoline derivatives were efficiently converted into vicinal diamines in microdroplets, while benzofused 7-membered N-heterocycles and minor imines were synthesized in bulk phase. A high flux approach enabled scaling up of the production of vicinal diamines to 177 mg per hour. By employing different synthetic methodologies for the same precursor, this study highlights the versatility of microdroplet chemistry for the discovery of novel molecules with high reaction selectivity, efficiency, substrate scope, and scalability in different reactors. The remarkable reactivity at the gas-organic interface enables good insights into gaswater and other interface-rich studies in atmospheric and photochemistry, on-water chemistry, biological and biomedical, industrial, and energy.