Ionic liquid/boronic acid system enabled deuteration with D2O

The development of transition-metal free systems for multi-sites deuteration is important for the preparation of deuterium-labeled drugs and intermediates. We reported that ionic liquid [bmim]PF6 was able to promote highly efficient deuterodeborylation of boronic acids with D2O. The ionic liquid/boronic acid system was successfully applied to the selective H/D exchange at various sp2/sp3 CH positions. Moreover, unusual nucleophilic behaviors of nitrogen-containing heteroaromatics in ionic liquid were observed.