Visible-light-induced radical 1,2-aryl migration in diaryl allyl alcohols for efficient synthesis of 1,5-dicarbonyl compounds

Herein, we developed a protocol for Ir(III)-photocatalyzed, visible-light-driven radical 1,2-aryl migration in diaryl allyl alcohols, leading to the formation of 1,5-dicarbonyl compounds under additive-free conditions, with broad substrate tolerance. Electron-deficient aryl groups exhibit enhanced migration efficiency compared to electron-rich or <i>ortho</i>-substituted analogs. Mechanistic studies implicated the formation of alkyl ester radical intermediates. This is a sustainable method that can be performed under mild conditions.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc02799c
Citations
3
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
2.81
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article

Visible-light-induced radical 1,2-aryl migration in diaryl allyl alcohols for efficient synthesis of 1,5-dicarbonyl compounds

Keyume Ablajan, Ping Jiang, Lijuan Li
3 citations
Chemical Communications
Radical Photochemical Reactions
2.81
article

Visible-light-induced radical 1,2-aryl migration in diaryl allyl alcohols for efficient synthesis of 1,5-dicarbonyl compounds

Keyume Ablajan, Ping Jiang, Lijuan Li
article en
3 citations

Abstract

Herein, we developed a protocol for Ir(III)-photocatalyzed, visible-light-driven radical 1,2-aryl migration in diaryl allyl alcohols, leading to the formation of 1,5-dicarbonyl compounds under additive-free conditions, with broad substrate tolerance. Electron-deficient aryl groups exhibit enhanced migration efficiency compared to electron-rich or <i>ortho</i>-substituted analogs. Mechanistic studies implicated the formation of alkyl ester radical intermediates. This is a sustainable method that can be performed under mild conditions.

Chemical CommunicationsVol. 61(69)
Xinjiang University (CN)
Openalex Percentile: Top 10%
Radical Photochemical Reactions
2.81
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