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February 8, 2026The Journal of Organic Chemistry3 citations

Photooxidation of Thioethers to Sulfoxides and the Self-Initiating Mechanism Evidenced by DFT Calculations

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QDQifu DengTZTingting ZhuSCShilin Chen

Key Points

  • The aim is to develop a catalyst-free method for the selective oxidation of thioethers into sulfoxides.
  • Developed a photoaerobic protocol for oxidation
  • Utilized acetic acid in the reaction
  • Conducted DFT calculations to identify mechanisms
  • Successfully synthesized alkyl-aryl, diaryl, and dialkyl sulfoxides
  • Confirmed the thioether-O2 complex acts as the photosensitizer
  • Achieved environmentally friendly synthesis of pharmaceutical compounds

Abstract

A catalyst-free photoaerobic protocol has been developed for the highly selective oxidation of thioethers in the presence of acetic acid. Based on DFT calculations, the thioether-O2 complex is identified as the photosensitizer to trigger the radical cascade. This protocol enables the green synthesis of alkyl-aryl, diaryl, and dialkyl sulfoxides, including pharmaceutical molecules.

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Cite This Study

Deng et al. (2026) studied this question.

synapsesocial.com/papers/6988270a0fc35cd7a8845f13https://doi.org/10.1021/acs.joc.5c02776
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