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Updated: Sep 17, 2025
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
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Visible-Light-Promoted Thioetherification Reactions via Electron Donor-Acceptor Complexes between Active Esters and
1Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China.
The Journal of Organic Chemistry
|July 2, 2025
Summary
Visible light promotes thioetherification using tetrachloro-N-hydroxyphthalimide esters (TCNHPI esters) and sulfinates. This method efficiently synthesizes alkyl aryl thioesters under mild conditions, offering a facile approach to valuable sulfide compounds.
Area of Science:
- Organic Chemistry
- Photochemistry
- Synthetic Chemistry
Background:
- Thioetherification reactions are crucial for synthesizing organic sulfides.
- Visible-light photocatalysis offers a sustainable alternative to traditional synthetic methods.
- Electron donor-acceptor (EDA) complexes can mediate photochemical transformations.
Purpose of the Study:
- To develop a novel visible-light-promoted thioetherification protocol.
- To synthesize alkyl aryl thioesters using readily available sulfinates.
- To elucidate the mechanism of the visible-light-driven reaction.
Main Methods:
- Utilizing tetrachloro-N-hydroxyphthalimide esters (TCNHPI esters) as photocatalysts.
- Employing sulfinates as sulfur sources in the presence of visible light.
- Characterizing the reaction mechanism through byproduct analysis, radical trapping, and spectroscopic studies (UV/Vis, fluorescence).
Main Results:
- Successful synthesis of 38 diverse alkyl aryl thioesters with yields up to 85%.
- Formation of a strong EDA complex between TCNHPI esters and sulfinates (KEDA = 584 M⁻¹).
- Confirmation of the reaction mechanism involving EDA complexes and radical intermediates.
Conclusions:
- A new, facile, and mild method for synthesizing sulfides from odorless sulfinates has been established.
- The protocol leverages visible-light photocatalysis and EDA complex formation.
- This approach provides an efficient route to valuable thioester compounds.
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