Tandem H/D Exchange-SET Reductive Deuteration Strategy for the Synthesis of α,β-Deuterated Amines Using D2O

α,β-Deuterated amines are crucial for the development of deuterated drugs. We intend to introduce the novel tandem H/D exchange-single electron transfer (SET) reductive deuteration strategy with high pot- and reagent-economy by the synthesis of α,β-deuterated amine using nitrile as the precursor. The H/D exchange of the −CH 2 CN group was achieved by D 2 O/Et 3 N, which were also the required reagents in the tandem SmI 2 -mediated SET reductive deuteration of the α-deuterated nitrile. The potential application of this method was further showcased by the synthesis of bevantolol- d 4 .