Chemical‐Reductant‐Free Electrochemical Deuteration Reaction using Deuterium Oxide

Abstract

We report am ethod for the electrochemical deuteration of a,b-unsaturated carbonyl compounds under catalystand external-reductant-free conditions,w ith deuteration rates as high as 99 %a nd yields up to 91 %i n2h. The use of graphite felt for both the cathode and the anode was key to ensuring chemoselectivity and high deuterium incorporation under neutral conditions without the need for an external reductant. This method has an umber of advantages over previously reported deuteration reactions that use stoichiometric metallic reductants.M echanistic experiments showed that O 2 evolution at the anode not only eliminates the need for an external reductant but also regulates the pH of the reaction mixture,keeping it approximately neutral.