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

doi:10.1055/s-0043-1775467

Synthesis, Inhaltsverzeichnis

Synthesis 2025; 57(13): 2124-2130
DOI: 10.1055/s-0043-1775467

paper

Bürgenstock Special Section 2023 – Future Stars in Organic Chemistry

Electro-Oxidative Platform for Nucleophilic α-Functionalization of Ketones

Rakesh Mondal‡

^aDepartment of Molecular Chemistry and Materials Science, The Weizmann Institute of Science, 7610001 Rehovot, Israel

,

Nicolas Jacob‡

^bMinakem Recherche, 145 Chemin des Lilas, 59310 Beuvry-la-Forêt, France

,

Maxime Devuyst

^bMinakem Recherche, 145 Chemin des Lilas, 59310 Beuvry-la-Forêt, France

,

Mathilde Quertenmont

^bMinakem Recherche, 145 Chemin des Lilas, 59310 Beuvry-la-Forêt, France

,

Gleb Averochkin

^aDepartment of Molecular Chemistry and Materials Science, The Weizmann Institute of Science, 7610001 Rehovot, Israel

,

Stav Deri

^aDepartment of Molecular Chemistry and Materials Science, The Weizmann Institute of Science, 7610001 Rehovot, Israel

,

Lior Galmidi

^aDepartment of Molecular Chemistry and Materials Science, The Weizmann Institute of Science, 7610001 Rehovot, Israel

,

Daniel Gordon-Levitan

^aDepartment of Molecular Chemistry and Materials Science, The Weizmann Institute of Science, 7610001 Rehovot, Israel

,

Moran Feller

^aDepartment of Molecular Chemistry and Materials Science, The Weizmann Institute of Science, 7610001 Rehovot, Israel

,

Julien C. Vantourout∗

^cSyngenta Crop Protection AG, Schaffauserstrasse, 4332 Stein, Switzerland

,

Pierre-Georges Echeverria ∗

^bMinakem Recherche, 145 Chemin des Lilas, 59310 Beuvry-la-Forêt, France

,

Samer Gnaim∗

^aDepartment of Molecular Chemistry and Materials Science, The Weizmann Institute of Science, 7610001 Rehovot, Israel

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Abstract

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Abstract

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 three 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.

Key words

electrosynthesis - alpha-functionalization of carbonyls - umpolung - electrochemistry - flow chemistry

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Referenzen

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