Photocatalytic Synthesis of Imidazoline and Oxazolidine Derivatives Using Organic Catalysts

Herein, we report a synthetic strategy that relies on a self‐developed organic photocatalyst for the efficient construction of imidazolines and oxazolidines. Using readily available 4‐methyl‐ N ‐(2‐phenylallyl)benzenesulfonamide alkenes and redox‐active esters (RAEs) or aryl diazonium tetrafluoroborates as substrates, the reaction proceeds in acetonitrile/acetone via photoredox‐initiated radical addition followed by ionic cyclization, which involves the formation of a key nitrilium/imidate‐type ionic intermediate. This transformation features mild reaction conditions and facile operation, not only expanding the application scope of the developed photocatalyst, but also providing a practical technical platform for the photocatalytic synthesis of structurally diverse bioactive molecules containing imidazoline and oxazolidine motifs.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2026-04-27
DOI
https://doi.org/10.1002/ejoc.70504
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Photocatalytic Synthesis of Imidazoline and Oxazolidine Derivatives Using Organic Catalysts

Yingjie Wang, Weijun Cao, Hui Zhang, Ke‐Chun Wang et al.
European Journal of Organic Chemistry
Radical Photochemical Reactions
article

Photocatalytic Synthesis of Imidazoline and Oxazolidine Derivatives Using Organic Catalysts

Yingjie Wang, Weijun Cao, Hui Zhang, Ke‐Chun Wang, Peng‐Fei Xu
article en

Abstract

Herein, we report a synthetic strategy that relies on a self‐developed organic photocatalyst for the efficient construction of imidazolines and oxazolidines. Using readily available 4‐methyl‐ N ‐(2‐phenylallyl)benzenesulfonamide alkenes and redox‐active esters (RAEs) or aryl diazonium tetrafluoroborates as substrates, the reaction proceeds in acetonitrile/acetone via photoredox‐initiated radical addition followed by ionic cyclization, which involves the formation of a key nitrilium/imidate‐type ionic intermediate. This transformation features mild reaction conditions and facile operation, not only expanding the application scope of the developed photocatalyst, but also providing a practical technical platform for the photocatalytic synthesis of structurally diverse bioactive molecules containing imidazoline and oxazolidine motifs.

European Journal of Organic Chemistry
Lanzhou Veterinary Research Institute (CN), Chinese Academy of Agricultural Sciences (CN), Lanzhou University (CN)
Openalex Percentile: Top 8%
Radical Photochemical Reactions
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