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Direct Vicinal Disubstitution of Diaryliodonium Salts by Pyridine N-oxides and N-amidates by a 1,3-Radical Rearrangement

Authors

  • Jing Peng,

    1. Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (China)
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  • Prof. Dr. Chao Chen,

    Corresponding author
    1. Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (China)
    • Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (China)
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  • Yong Wang,

    1. Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (China)
    2. College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042 (China)
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  • Zhenbang Lou,

    1. Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (China)
    2. College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042 (China)
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  • Prof. Dr. Ming Li,

    1. College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042 (China)
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  • Prof. Dr. Chanjuan Xi,

    1. Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (China)
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  • Prof. Dr. Hui Chen

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (China)
    • Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (China)
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  • This work was supported by the National Natural Science Foundation of China (21102080 and 21290194), the Tsinghua University Initiative Scientific Research Program (2011Z02150), and the Chinese Academy of Sciences.

Abstract

original image

Paired off: The title reaction leads to a series of o-pyridinium phenols (1) and anilines (2). The experimental and computational studies indicate that the key step involves homolytic cleavage to give a radical pair, which undergoes solvent-cage recombination to give the product.

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