Electro-Oxidative Platform for Nucleophilic α-Functionalization of Ketones

    Rakesh Mondal, Nicolas Jacob, Maxime Devuyst, Mathilde Quertenmont, Gleb Averochkin, Stav Deri, Lior Galmidi, Daniel Gordon-Levitan, Moran Feller, Julien C. Vantourout, Pierre-Georges Echeverria, Samer Gnaim

    • Weizmann Institute of Science

    The significance of α-functionalization of carbonyl compounds arises from its frequent use in synthetic organic chemistry. Consequently, there is a substantial and constant demand for the creation of strategies that facilitate the efficient execution of such valuable transformation. In this context, herein is presented a universal electrochemical oxidative platform for the α- derivatization of ketones with nucleophiles, employing an umpolung reactivity. This approach has been successfully employed in five distinct transformations involving C-C and C-X bond formation via straightforward nucleophilic substitution or cycloaddition reaction pathways. Furthermore, the implementation of this methodology in flow using a commercially available reactor demonstrated its inherent scalability.

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