Synthesis of 1,4‐Dicarbonyl Compounds by Visible‐Light‐Mediated Cross‐Coupling Reactions of α‐Chlorocarbonyls and Enol Acetates

Herein, we report a protocol for visible‐light‐mediated radical coupling reactions of α‐chloroketones and enol acetates to afford 1,4‐dicarbonyl compounds, which are important precursors and intermediates in organic synthesis. The reaction involves photoredox‐catalyzed activation of the α‐chloroketo...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2020-10, Vol.362 (20), p.4391-4396
Main Authors: Liu, Qiang, Wang, Rui‐Guo, Song, Hong‐Jian, Liu, Yu‐Xiu, Wang, Qing‐Min
Format: Article
Language:English
Subjects:
1,4-Dicarbonyl compounds
Acetates
Carbon
Carbonyl compounds
Chemical reactions
Chemical synthesis
Chlorine
Coupling (molecular)
Cross coupling
Photocatalysis
Photoelectrons
Substrates
Unsymmetrical diketones
α-Chlorocarbonyls
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Summary:Herein, we report a protocol for visible‐light‐mediated radical coupling reactions of α‐chloroketones and enol acetates to afford 1,4‐dicarbonyl compounds, which are important precursors and intermediates in organic synthesis. The reaction involves photoredox‐catalyzed activation of the α‐chloroketone upon photoelectron transfer, carbon–chlorine bond cleavage, and coupling of the resulting radical with the carbon–carbon double bond of the enol acetate. This mild protocol has a wide substrate scope and moderate to good yields.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000791