MR. SHUAIZHONG ZHANG

The promising application of deuterium-labeled compounds, such as the drug deutetrabenazine, warrants efficient, selective, and direct deuteration of organic entities. We here present a highly effective regioselective direct C–H deuteration of indole in D2O using Cp*Co(CO)I2, [Cp*RhCl2]2, or their combination as a catalyst. This transition-metal-catalyzed system made available mono(C2)-, di(C2/C7)-, tri(C2/C3/C7)-, and even C4-deuterated products from diverse indole substrates, equipped with the removable N1-directing group. The selective H/D exchanges on the rest sites of indoles were also realized by shifting the directing group. Furthermore, an example of this approach was demonstrated to acquire deuteromelatonin from the drug melatonin.