Ag₂CO₃-Catalyzed H/D Exchange of Five-Membered Heteroarenes at Ambient Temperature

Ag₂CO₃-catalyzed hydrogen isotope exchange of five-membered heteroarenes is disclosed. The reaction can be conducted in the open air, at ambient temperature, and with D₂O as deuterium source. Moreover, this protocol showed orthogonal site selectivity to existing technology, thereby greatly expanding the scope of substrates for HIE reaction. The mechanistic study indicated that the carbonate group plays a crucial role to achieve high levels of deuterium incorporation by lowering the activation energy of H/D exchange process.