Fig. 2: Electrochemically driven dehalogenative deuteration of unactivated alkyl halides.

Electrochemically driven dehalogenative deuteration of unactivated alkyl halides. A Scope of alkyl bromides, B scope of alkyl iodides, C scope of alkylchlorides, and D complex biologically important substrates. ^aReaction conditions: bromide, iodide or pseudo-halides (0.5 mmol), D₂O (25 mmol), TBAI (20 mol %), DIPEA (1.5 mmol), DMF (5.0 mL) under 30 mA constant current in an undivided cell at room temperature for 10 h with carbon felt as anode and lead plate as cathode. Isolated yield of product. Deuterium incorporation determined by ¹H NMR. ^bAlkyl chlorides (0.5 mmol) was conducted under 50 mA constant current with graphite felt as anode. ^cDeuterium incorporation determined by GC-MS.