Electrochemical low valent cobalt-catalyzed addition of aryl and vinyl chlorides to α-ketoamides via C–Cl bond activation

Prashant S. Shinde; Valmik S. Shinde; Magnus Rueping

doi:10.1039/D4CC00309H

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Electrochemical low valent cobalt-catalyzed addition of aryl and vinyl chlorides to α-ketoamides via C–Cl bond activation†

Prashant S. Shinde,^a Valmik S. Shinde*^ab and Magnus Rueping

*^a

Author affiliations

* Corresponding authors

^a King Abdullah University of Science and Technology (KAUST), KAUST Catalysis Center (KCC), Thuwal 23955-6900, Saudi Arabia
E-mail: magnus.rueping@kaust.edu.sa

^b Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, Uttar Pradesh, India
E-mail: valmik.shinde@cdri.res.in

Abstract

The development of an electrochemical cobalt catalyzed C–Cl bond activation at room temperature for the nucleophilic addition of aryl and vinyl chlorides to α-ketoamides is described. The overall method operates through an electrochemically induced low valent cobalt catalyst that oxidatively adds to aryl or vinyl chlorides affording medicinally important 3-hydroxy oxindole and 3-hydroxypyrrolidinone scaffolds. The development of an enantioselective version using a chiral pyrox ligand is also demonstrated.

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Article information

DOI: https://doi.org/10.1039/D4CC00309H
Article type: Communication
Submitted: 22 Jan 2024
Accepted: 06 Mar 2024
First published: 18 Mar 2024
This article is Open Access

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Chem. Commun., 2024,60, 3826-3829

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Electrochemical low valent cobalt-catalyzed addition of aryl and vinyl chlorides to α-ketoamides via C–Cl bond activation

P. S. Shinde, V. S. Shinde and M. Rueping, Chem. Commun., 2024, 60, 3826 DOI: 10.1039/D4CC00309H

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Chemical Communications

Electrochemical low valent cobalt-catalyzed addition of aryl and vinyl chlorides to α-ketoamides via C–Cl bond activation†

Abstract

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Electrochemical low valent cobalt-catalyzed addition of aryl and vinyl chlorides to α-ketoamides via C–Cl bond activation

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