Eosin Y-Photocatalyzed α-Hydroxy-β-sulfinylation/sulfenylation of α-(Trifluoromethyl)styrenes

This study demonstrates an eosin Y (EY)-photocatalyzed α-hydroxy-β-sulfinylation of α-(trifluoromethyl)styrenes with thiophenols, enabling the efficient synthesis of valuable α-trifluoromethyl-β-sulfinyl tertiary alcohols. Notably, when heterocyclic thiols are used, the reaction selectively affords α-trifluoromethyl-β-thioether tertiary alcohols via α-hydroxy-β-sulfenylation. The developed methodology features a broad substrate scope, excellent functional group compatibility, and high chemoselectivity. From a green chemistry perspective, this protocol showcases distinct advantages: it utilizes visible light as an energy source and EY as a photocatalyst, operates under transition metal-free conditions, employs air as the oxidant, and demonstrates high atom economy, providing a sustainable platform for the sulfenylation/sulfenylation of bioactive molecules.

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Publication Details

Journal
ACS Sustainable Chemistry & Engineering
Published
2026-03-13
DOI
https://doi.org/10.1021/acssuschemeng.5c07017
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Eosin Y-Photocatalyzed α-Hydroxy-β-sulfinylation/sulfenylation of α-(Trifluoromethyl)styrenes

Qingle Zeng, Yi Cao, Lei Shen
ACS Sustainable Chemistry & Engineering
Sulfur-Based Synthesis Techniques
article

Eosin Y-Photocatalyzed α-Hydroxy-β-sulfinylation/sulfenylation of α-(Trifluoromethyl)styrenes

Qingle Zeng, Yi Cao, Lei Shen
article en

Abstract

This study demonstrates an eosin Y (EY)-photocatalyzed α-hydroxy-β-sulfinylation of α-(trifluoromethyl)styrenes with thiophenols, enabling the efficient synthesis of valuable α-trifluoromethyl-β-sulfinyl tertiary alcohols. Notably, when heterocyclic thiols are used, the reaction selectively affords α-trifluoromethyl-β-thioether tertiary alcohols via α-hydroxy-β-sulfenylation. The developed methodology features a broad substrate scope, excellent functional group compatibility, and high chemoselectivity. From a green chemistry perspective, this protocol showcases distinct advantages: it utilizes visible light as an energy source and EY as a photocatalyst, operates under transition metal-free conditions, employs air as the oxidant, and demonstrates high atom economy, providing a sustainable platform for the sulfenylation/sulfenylation of bioactive molecules.

ACS Sustainable Chemistry & Engineering
Chengdu University of Technology (CN)
Clean water and sanitation
Openalex Percentile: Top 22%
Sulfur-Based Synthesis Techniques
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