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

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

Department of Molecular Chemistry and Materials Science

Weizmann Institute of Science

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Article number	SS-2024-12-0486-OP
Journal	Synthesis
Early online date	9 Apr 2025
DOIs	https://doi.org/10.1055/s-0043-1775467
State	Published Online - 9 Apr 2025

Keywords

alpha-functionalization of carbonyls
electrochemistry
electrosynthesis
flow chemistry
umpolung

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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10.1055/s-0043-1775467

Cite this

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title = "Electro-Oxidative Platform for Nucleophilic α-Functionalization of Ketones",

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.",

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

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doi = "10.1055/s-0043-1775467",

language = "الإنجليزيّة",

journal = "Synthesis",

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TY - JOUR

T1 - Electro-Oxidative Platform for Nucleophilic α-Functionalization of Ketones

AU - Mondal, Rakesh

AU - Jacob, Nicolas

AU - Devuyst, Maxime

AU - Quertenmont, Mathilde

AU - Averochkin, Gleb

AU - Deri, Stav

AU - Galmidi, Lior

AU - Gordon-Levitan, Daniel

AU - Feller, Moran

AU - Vantourout, Julien C.

AU - Echeverria, Pierre Georges

AU - Gnaim, Samer

PY - 2025/4/9

Y1 - 2025/4/9

N2 - 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.

AB - 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.

KW - alpha-functionalization of carbonyls

KW - electrochemistry

KW - electrosynthesis

KW - flow chemistry

KW - umpolung

UR - http://www.scopus.com/inward/record.url?scp=105003165117&partnerID=8YFLogxK

U2 - 10.1055/s-0043-1775467

DO - 10.1055/s-0043-1775467

M3 - مقالة

SN - 0039-7881

JO - Synthesis

JF - Synthesis

M1 - SS-2024-12-0486-OP

ER -

Electro-Oxidative Platform for Nucleophilic α-Functionalization of Ketones

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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