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Anti-Markovnikov ring-opening of sulfonium salts with alkynes by visible light/copper catalysis

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Abstract

Internal alkynes are widespread skeletons in bioactive molecules and materials which are also used as important building blocks in chemical synthesis. Herein, we report a novel and efficient copper-catalyzed Sonogashira reaction between sulfonium salts and alkynes through an anti-Markovnikov ring-opening pathway promoted by visible light. The coexistence of the nitrogen and phosphorus ligands in the system is the key to the success of this reaction. This radical type ring-opening reaction affords a new strategy for the synthesis of internal alkynes. Furthermore, this study is also an effective complement to the diverse reaction patterns of sulfonium salts.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22271170) and the Scientific Research Foundation of Qingdao University of Science and Technology (1203043003457).

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Authors and Affiliations

  1. Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science, Ministry Of Education, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China

    Xuan Li, Junze Zuo, Xiuyan Song, Jian Lv & Daoshan Yang

  2. College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 310036, China

    Min Jiang

  3. Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, 100084, China

    Daoshan Yang

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  1. Xuan Li
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  2. Min Jiang
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Li, X., Jiang, M., Zuo, J. et al. Anti-Markovnikov ring-opening of sulfonium salts with alkynes by visible light/copper catalysis. Sci. China Chem. 66, 791–798 (2023). https://doi.org/10.1007/s11426-022-1373-y

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