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Photocatalyzed ditrifluoromethylthiolation of alkenes with CF3SO2Na

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Abstract

Since the first report of sodium trifluoromethanesulfinate (CF3SO2Na) as an electrophilic trifluoromethylthiolation reagent in 2015, there has been no breakthrough in research in this field. Herein, we disclose an unprecedented usage of CF3SO2Na as a radical trifluoromethylthiolation reagent. A photocatalyzed ditrifluoromethylthiolation of alkenes with CF3SO2Na in the presence of PPh3 and catalytic copper has been developed. Interestingly, either Ir[(p-Fppy)2(bpy)]PF6 or Ir(ppy)3 could facilitate this transformation. Mechanistic studies indicate that initiation of the radical chain proceeded via two different photocatalytic quenching mechanisms. This protocol provides a practical method for the construction of diverse vicinal ditrifluoromethylthiolated compounds.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22078161, 22108124), the Postdoctoral Science Foundation Funded Project (2019M661848), the Fundamental Research Funds for the Central Universities (30922010403), the Priority Academic Program Development of Jiangsu Higher Education Institutions, and the Center for Advanced Materials and Technology in Nanjing University of Science and Technology.

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Author notes

  1. These authors contributed equally to this work.

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, China

    Fangming Chen, Lvqi Jiang, Chunyang Hu, Jie Liu & Wenbin Yi

  2. Key Laboratory of Organofluorine Chemistry, Shanghai Institute Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

    Wenbin Yi

Authors
  1. Fangming Chen
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  2. Lvqi Jiang
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  3. Chunyang Hu
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  4. Jie Liu
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Correspondence to Lvqi Jiang, Jie Liu or Wenbin Yi.

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Conflict of interest The authors declare no conflict of interest.

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Supporting information The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Chen, F., Jiang, L., Hu, C. et al. Photocatalyzed ditrifluoromethylthiolation of alkenes with CF3SO2Na. Sci. China Chem. 67, 587–594 (2024). https://doi.org/10.1007/s11426-023-1781-6

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  • DOI: https://doi.org/10.1007/s11426-023-1781-6

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