Visible Light instead of Transition Metal: Electron Donor Acceptor Complex Enabled Cross‐Coupling of Aryl Halides with Active Methylene Compounds

An arylation of anions of active methylene compounds with aryl halides provides an access to synthetically versatile α‐arylated 1,3‐diketones, β‐keto esters, β‐keto nitriles, β‐cyano esters, etc. Previously, these C−C cross‐coupling reactions have been accomplished only using transition metal‐based...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-02, Vol.366 (3), p.457-464
Main Authors: Volkov, Alexey A., Bugaenko, Dmitry I., Karchava, Alexander V.
Format: Article
Language:English
Subjects:
Aromatic compounds
Catalysts
Chemical reactions
Cross coupling
C−C coupling
Diketones
Electron transfer
Esters
Halides
Methylene
Nitriles
Photochemistry
Radical reactions
Synthetic methods
Transition metals
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Summary:An arylation of anions of active methylene compounds with aryl halides provides an access to synthetically versatile α‐arylated 1,3‐diketones, β‐keto esters, β‐keto nitriles, β‐cyano esters, etc. Previously, these C−C cross‐coupling reactions have been accomplished only using transition metal‐based catalysts. Herein, we demonstrate that these arylations can be successfully realized under catalyst‐free conditions employing the electron donor‐acceptor (EDA) complex photoactivation strategy. The protocol was further optimized for a semi‐one pot synthesis of indole derivatives via an intramolecular C−C coupling.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202301192