Light‐Mediated Decomposition of Arylseleninic Acids in Aqueous Medium: A Green Alternative Toward Organoselenium‐Functionalized Imidazo[1,2‐ <i>a</i> ]pyridines

Abstract In the present work, a mild protocol was developed to construct 2‐aryl‐3‐(arylselanyl)imidazo[1,2‐ a ]pyridines, under blue light irradiation, employing benzeneseleninic acid derivatives as a Se(II) source. The experimental design approach (design of experiment, DoE) was used to establish the best reaction conditions, which delivered fourteen derivatives in moderate to good yields (23%–75%), after reacting for 24–48 h. Furthermore, the developed method proved to be efficient when increasing the reaction scale (2.5 mmol), which provided the desired product in 70% yield (0.61 g) after 24 h of reaction, demonstrating the applicability of this method on a preparative scale. The present approach does not require the use of metals, strong oxidants, or heating, in addition to producing only H 2 O and diaryl diselenide as byproducts, which can be recovered and reused.

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2025-06-21
DOI
https://doi.org/10.1002/ajoc.202500442
Primary Topic
Organoselenium and organotellurium chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Light‐Mediated Decomposition of Arylseleninic Acids in Aqueous Medium: A Green Alternative Toward Organoselenium‐Functionalized Imidazo[1,2‐ a ]pyridines

João M. Anghinoni, Márcio S. Silva, Filipe Penteado, Caroline Signorini Gomes et al.
Asian Journal of Organic Chemistry
Organoselenium and organotellurium chemistry
article

Light‐Mediated Decomposition of Arylseleninic Acids in Aqueous Medium: A Green Alternative Toward Organoselenium‐Functionalized Imidazo[1,2‐ a ]pyridines

João M. Anghinoni, Márcio S. Silva, Filipe Penteado, Caroline Signorini Gomes, Sabrina S. Ferreira, Carolina Aires de Oliveira, Eder J. Lenardão
article en

Abstract

Abstract In the present work, a mild protocol was developed to construct 2‐aryl‐3‐(arylselanyl)imidazo[1,2‐ a ]pyridines, under blue light irradiation, employing benzeneseleninic acid derivatives as a Se(II) source. The experimental design approach (design of experiment, DoE) was used to establish the best reaction conditions, which delivered fourteen derivatives in moderate to good yields (23%–75%), after reacting for 24–48 h. Furthermore, the developed method proved to be efficient when increasing the reaction scale (2.5 mmol), which provided the desired product in 70% yield (0.61 g) after 24 h of reaction, demonstrating the applicability of this method on a preparative scale. The present approach does not require the use of metals, strong oxidants, or heating, in addition to producing only H 2 O and diaryl diselenide as byproducts, which can be recovered and reused.

Asian Journal of Organic ChemistryVol. 14(8)
Universidade Federal de Pelotas (BR), Universidade Federal de Santa Maria (BR)
Coordenação de Aperfeiçoamento de Pessoal de Nível Superior, Conselho Nacional de Desenvolvimento Científico e Tecnológico, Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul, Financiadora de Estudos e Projetos
Openalex Percentile: Top 86%
Organoselenium and organotellurium chemistry
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Light‐Mediated Decomposition of Arylseleninic Acids in Aqueous Medium: A Green Alternative Toward Organoselenium‐Functionalized Imidazo[1,2‐ <i>a</i> ]pyridines — João M. Anghinoni, Márcio S. Silva, et al. · Asian Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS