Visible-light-promoted hydroxysulfenylation of alkenes for the synthesis of β-hydroxysulfides

Herein, we report a regioselective, visible-light-activated and base-catalyzed difunctionalized strategy for the preparation of β-hydroxysulfides from alkenes, thiols, and molecular oxygen (O<sub>2</sub>). This one-pot, metal- and photocatalyst-free transformation offers an efficient and straightforward approach to access β-hydroxysulfides under environmentally-friendly conditions. This reaction features a broad substrate scope, excellent functional group tolerance, and good to excellent isolated yields (up to 94%), and uses molecular oxygen as a green oxidant, making it valuable for applications in synthetic organic chemistry. Detailed spectroscopic studies (such as UV-Vis, NMR, EPR, and HRMS analyses), along with several control experiments, provide a deeper mechanistic understanding of the transformation, thereby enhancing the significance of this work.

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Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob01424g
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Visible-light-promoted hydroxysulfenylation of alkenes for the synthesis of β-hydroxysulfides

Chin‐Fa Lee, Rekha Bai, Yang Jian, Shih-Jie Chen et al.
Organic & Biomolecular Chemistry
Sulfur-Based Synthesis Techniques
article

Visible-light-promoted hydroxysulfenylation of alkenes for the synthesis of β-hydroxysulfides

Chin‐Fa Lee, Rekha Bai, Yang Jian, Shih-Jie Chen, Indrajit Karmakar
article en

Abstract

Herein, we report a regioselective, visible-light-activated and base-catalyzed difunctionalized strategy for the preparation of β-hydroxysulfides from alkenes, thiols, and molecular oxygen (O<sub>2</sub>). This one-pot, metal- and photocatalyst-free transformation offers an efficient and straightforward approach to access β-hydroxysulfides under environmentally-friendly conditions. This reaction features a broad substrate scope, excellent functional group tolerance, and good to excellent isolated yields (up to 94%), and uses molecular oxygen as a green oxidant, making it valuable for applications in synthetic organic chemistry. Detailed spectroscopic studies (such as UV-Vis, NMR, EPR, and HRMS analyses), along with several control experiments, provide a deeper mechanistic understanding of the transformation, thereby enhancing the significance of this work.

Organic & Biomolecular ChemistryVol. 23(46)
National Chung Hsing University (TW)
Openalex Percentile: Top 76%
Sulfur-Based Synthesis Techniques
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Visible-light-promoted hydroxysulfenylation of alkenes for the synthesis of β-hydroxysulfides — Chin‐Fa Lee, Rekha Bai, et al. · Organic & Biomolecular Chemistry (2025) | TGRS Research Map | TGRS