Visible‐Light‐Promoted Dearomatization for The Construction of Imidazole Scaffolds

Dearomatization is a powerful strategy for constructing complex carbocycles and heterocycles, though it typically relies on harsh conditions due to aromatic stability. Herein, a visible‐light‐driven photocatalytic dearomatization strategy for electron‐poor imidazo[1,2‐ a ]pyridines is reported, addressing a key limitation of current methods, which predominantly target electron‐rich aromatic systems. Using α ‐keto acids as acyl radical precursors, this mild method enables the efficient synthesis of structurally diverse and functionalized imidazole derivatives, a privileged scaffold in pharmaceuticals and advanced materials. Some of the synthesized imidazoles display noteworthy photophysical properties. Some of the synthesized imidazoles show dual fluorescence from deep violet to greenish‐cyan, highlighting potential as innovative fluorescent probes. This work expands the scope of dearomatization and provides a valuable tool for accessing new chemical space in drug discovery and materials science.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2025-08-21
DOI
https://doi.org/10.1002/adsc.70084
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Visible‐Light‐Promoted Dearomatization for The Construction of Imidazole Scaffolds

Silvia Roscales, Aurelio G. Csákÿ
Advanced Synthesis & Catalysis
Radical Photochemical Reactions
article

Visible‐Light‐Promoted Dearomatization for The Construction of Imidazole Scaffolds

Silvia Roscales, Aurelio G. Csákÿ
article en

Abstract

Dearomatization is a powerful strategy for constructing complex carbocycles and heterocycles, though it typically relies on harsh conditions due to aromatic stability. Herein, a visible‐light‐driven photocatalytic dearomatization strategy for electron‐poor imidazo[1,2‐ a ]pyridines is reported, addressing a key limitation of current methods, which predominantly target electron‐rich aromatic systems. Using α ‐keto acids as acyl radical precursors, this mild method enables the efficient synthesis of structurally diverse and functionalized imidazole derivatives, a privileged scaffold in pharmaceuticals and advanced materials. Some of the synthesized imidazoles display noteworthy photophysical properties. Some of the synthesized imidazoles show dual fluorescence from deep violet to greenish‐cyan, highlighting potential as innovative fluorescent probes. This work expands the scope of dearomatization and provides a valuable tool for accessing new chemical space in drug discovery and materials science.

Advanced Synthesis & CatalysisVol. 367(20)
Universidad Complutense de Madrid (ES)
Ministerio de Ciencia e Innovación
Openalex Percentile: Top 84%
Radical Photochemical Reactions
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Visible‐Light‐Promoted Dearomatization for The Construction of Imidazole Scaffolds — Silvia Roscales, Aurelio G. Csákÿ · Advanced Synthesis & Catalysis (2025) | TGRS Research Map | TGRS