Site‐selective Hydrogenation/Deuteration of Benzylic Olefins Enabled by Electroreduction Using Water

Abstract

Abstract We describe an operationally simple and user‐friendly protocol that allows the site‐selective hydrogenation and deuteration of di‐, tri‐ and tetrasubstituted benzylic olefins by electroreduction while other groups prone to hydrogenation are present. The radical anionic intermediates react with the most inexpensive hydrogen/deuterium source H 2 O/D 2 O. Our method overcomes many limitations that arise from previously reported electroreductive hydrogenations. The applicability of this reaction is demonstrated by a broad substrate scope (>50 examples) that focuses on functional group tolerance and sites that are affected by metal‐catalyzed hydrogenation (alkenes, alkynes, protecting groups).

Topics & Concepts