Reductive Deuteration of Nitriles: The Synthesis of α,α-Dideuterio Amines by Sodium-Mediated Electron Transfer Reactions.

The first general reductive deuteration of nitriles under single-electron transfer conditions has been developed for the synthesis of α,α-dideuterio amines. This practical and cost-efficient protocol requires only bench stable and commercially available sodium dispersions and EtOD- d1 and allows for the reductive deuteration of a variety of nitriles in excellent yields and deuterium incorporations.