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Photocatalyst-controlled and visible light-enabled selective oxidation of pyridinium salts

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Abstract

This study proposes two different methods of photocatalytic-controlled and visible light-induced selective oxidation of pyridiniums with air as the terminal oxidant. The key to these transformations is to choose the appropriate light source and photocatalyst. Pyridiniums are successfully converted into pyrroles through oxygen-mediated cycloaddition, proton-coupled electron transfer (PCET), pyridine ring opening, and recyclization. The other route is that pyridiniums selectively form 4-carbonyl pyridines through free radical rearrangement/aerobic oxidation under the catalysis of cobalt (II).

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22061003, 21861006), the Guangxi Natural Science Foundation of China (2016GXNSFEA380001, 2019GXNSFAA245027), the Guangxi Key R&D Program (AB18221005), the Science and Technology Major Project of Guangxi (AA17204058-21) and Guangxi Science and Technology Base and Special Talents (guike AD19110027).

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Authors and Affiliations

  1. State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin, 541004, China

    Xiang-Jun Peng, Kun She, Bao-Qi Zhang, Heng-Shan Wang, Hai-Tao Tang & Ying-Ming Pan

  2. Key Laboratory of Prevention and Treatment of Cardiovascular and Cerebrovascular Diseases of Ministry of Education, Gannan Medical University, Ganzhou, 341000, China

    Xiang-Jun Peng, Hai-Ping He & Qian Liu

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  1. Xiang-Jun Peng
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Correspondence to Heng-Shan Wang, Hai-Tao Tang or Ying-Ming Pan.

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Peng, XJ., He, HP., Liu, Q. et al. Photocatalyst-controlled and visible light-enabled selective oxidation of pyridinium salts. Sci. China Chem. 64, 753–760 (2021). https://doi.org/10.1007/s11426-020-9958-6

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  • DOI: https://doi.org/10.1007/s11426-020-9958-6

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