Key Intermediates of Iodine-Mediated Electrophilic Cyclization: Isolation and Characterization in an Osmabenzene System

Authors

  • Tongdao Wang,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, and State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen, 361005 (China)
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    • These authors contributed equally to this work.

  • Dr. Hong Zhang,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, and State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen, 361005 (China)
    2. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon (Hong Kong)
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    • These authors contributed equally to this work.

  • Feifei Han,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, and State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen, 361005 (China)
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  • Lipeng Long,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, and State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen, 361005 (China)
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  • Prof. Dr. Zhenyang Lin,

    Corresponding author
    1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon (Hong Kong)
    • Zhenyang Lin, Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon (Hong Kong)

      Haiping Xia, Department of Chemistry, College of Chemistry and Chemical Engineering, and State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen, 361005 (China)

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  • Prof. Dr. Haiping Xia

    Corresponding author
    1. Department of Chemistry, College of Chemistry and Chemical Engineering, and State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen, 361005 (China)
    • Zhenyang Lin, Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon (Hong Kong)

      Haiping Xia, Department of Chemistry, College of Chemistry and Chemical Engineering, and State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen, 361005 (China)

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  • We thank the 973 Program (No. 2012CB821600), the National Natural Science Foundation of China (20925208, 21174115, 21272193), the Research Grants Council of Hong Kong (HKUST603711), and program for Changjiang Scholars and Innovative Research Team in University.

Abstract

original image

Caught in the act: Key intermediates in an iodine-mediated electrophilic cyclization reaction was isolated by introducing metallabenzenes as the starting material. The unique structure of the intermediate should be described as the intimate ion pair form, instead of the widely accepted iodonium ion form.

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