B(C 6 F 5 ) 3 -Catalyzed Regioselective Deuteration of Electron-Rich Aromatic and Heteroaromatic Compounds.

Deuterium labeled compounds find widespread application in life science. Herein, the deuteration of electron-rich (hetero)aromatic compounds employing B(C6 F5 )3 as the catalyst and D2 O as the deuterium source is reported. This protocol is highly efficient, simply manipulated, and successfully applied in the deuteration of 23 substrates including natural neurotransmitter-like melatonin. It is assumed that the weakening of the O-D bond ultimately results in the formation of electrophilic D+ .