Cobalt‐Catalyzed Highly Regioselective Three‐Component Arylcarboxylation of Acrylate with Aryl Bromides and Carbon Dioxide

Cobalt‐catalyzed regioselective three‐component arylcarboxylation of acrylate with aryl bromides and carbon dioxide has been developed. The reaction is carried out by using cobalt chloride as a precatalyst and zinc powder as a reducing reagent under CO2 (1 atm) at 40 °C. A range of aryl bromides are...

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Bibliographic Details
Published in:ChemSusChem 2021-11, Vol.14 (22), p.4941-4946
Main Authors: Hang, Wei, Liang, Nianjie, Liu, Yuzhou, Xi, Chanjuan
Format: Article
Language:English
Subjects:
Aromatic compounds
arylcarboxylation
Bromides
Carbon dioxide
Carboxylic acids
Chemical reduction
Cobalt
enolates
homogeneous catalysis
Reagents
Regioselectivity
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Summary:Cobalt‐catalyzed regioselective three‐component arylcarboxylation of acrylate with aryl bromides and carbon dioxide has been developed. The reaction is carried out by using cobalt chloride as a precatalyst and zinc powder as a reducing reagent under CO2 (1 atm) at 40 °C. A range of aryl bromides are used for this reaction, leading to a series of valuable carboxylic acids with high regioselectivity and functional‐group compatibility. Mechanistic experiments and DFT calculations indicate that this arylcarboxylation reaction involves the reaction of CO2 with a cobalt enolate intermediate to form the C−C bond. Cobalt‐catalyzed reductive arylcarboxylation of t‐butyl acrylate is demonstrated with electrophilic aryl bromides and carbon dioxide, cheap cobalt chloride as precatalyst, and zinc dust as a reductant. The reaction has excellent regioselectivity and functional‐group compatibility and is suitable for a range of aryl bromides.
ISSN:1864-5631
1864-564X
DOI:10.1002/cssc.202101963