Visible Light-Mediated Synthesis of Chalcogen-Decorated 2,3-Dihydrobenzofurans in the Absence of Photocatalyst and Oxidants

A sustainable visible light-promoted protocol for preparing selenium- and sulfur-decorated 2,3-dihydrobenzofurans from 2-allylphenols and diorganyl dichalcogenides is reported. The reaction proceeds under blue LEDs irradiation (Kessil PR160L, λ<sub>max</sub> = 440 nm) under mild conditions, in the absence of photocatalysts or oxidants, in accordance with the green chemistry principles. Eighteen derivatives were obtained, covering electron-rich, electron-deficient, and polycyclic systems, with yields from 20% to 96%. The method is operationally simple, scalable, and tolerant to diverse aryl substituents, although the presence of electron-withdrawing groups reduces its efficiency. This approach offers an ecofriendly alternative to conventional oxidative or photocatalyst-mediated strategies to prepare the target molecules, opening new opportunities for advancing organoselenium chemistry and exploring its potential in organic synthesis.

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Publication Details

Journal
ACS Omega
Published
2026-03-04
DOI
https://doi.org/10.1021/acsomega.5c12021
Primary Topic
Organoselenium and organotellurium chemistry
Type
article
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article

Visible Light-Mediated Synthesis of Chalcogen-Decorated 2,3-Dihydrobenzofurans in the Absence of Photocatalyst and Oxidants

Gelson Perin, Ricardo Frederico Schumacher, Filipe Penteado, Sabrina S. Ferreira et al.
ACS Omega
Organoselenium and organotellurium chemistry
article

Visible Light-Mediated Synthesis of Chalcogen-Decorated 2,3-Dihydrobenzofurans in the Absence of Photocatalyst and Oxidants

Gelson Perin, Ricardo Frederico Schumacher, Filipe Penteado, Sabrina S. Ferreira, Mateus W. Rambo, Eder J. Lenardão, Thiago Anjos, Guilherme Araújo
article en

Abstract

A sustainable visible light-promoted protocol for preparing selenium- and sulfur-decorated 2,3-dihydrobenzofurans from 2-allylphenols and diorganyl dichalcogenides is reported. The reaction proceeds under blue LEDs irradiation (Kessil PR160L, λ<sub>max</sub> = 440 nm) under mild conditions, in the absence of photocatalysts or oxidants, in accordance with the green chemistry principles. Eighteen derivatives were obtained, covering electron-rich, electron-deficient, and polycyclic systems, with yields from 20% to 96%. The method is operationally simple, scalable, and tolerant to diverse aryl substituents, although the presence of electron-withdrawing groups reduces its efficiency. This approach offers an ecofriendly alternative to conventional oxidative or photocatalyst-mediated strategies to prepare the target molecules, opening new opportunities for advancing organoselenium chemistry and exploring its potential in organic synthesis.

ACS OmegaVol. 11(10)
Universidade Federal de Pelotas (BR), Universidade Federal de Santa Maria (BR), Instituto de Ciências Farmacêuticas (BR)
Responsible consumption and production
Openalex Percentile: Top 43%
Organoselenium and organotellurium chemistry
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