Magnesium-Promoted Reductive Carboxylation of Aryl Vinyl Ketones: Synthesis of γ‑Keto Carboxylic Acids

Direct reductive carboxylation of easily prepared aryl vinyl ketones under the atmosphere of carbon dioxide led to the selective formation of γ-keto carboxylic acids in 38–86% yields. The reaction is characterized by the carbon–carbon bond formation of carbon dioxide at the β-position of enone, with...

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Veröffentlicht in:Journal of organic chemistry 2022-06, Vol.87 (11), p.7342-7349
Hauptverfasser: Zheng, Suhua, Zhang, Tianyuan, Maekawa, Hirofumi
Format: Artikel
Sprache:eng
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Zusammenfassung:Direct reductive carboxylation of easily prepared aryl vinyl ketones under the atmosphere of carbon dioxide led to the selective formation of γ-keto carboxylic acids in 38–86% yields. The reaction is characterized by the carbon–carbon bond formation of carbon dioxide at the β-position of enone, with the use of magnesium turnings that can be easily handled as the reducing agent and the eco-friendly reaction conditions such as no pressuring, no lower or higher reaction temperature, and short reaction time. This protocol showed a wide substrate scope and provided a useful and convenient alternative to access biologically important γ-keto carboxylic acids.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00557