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Dearomative di- and trifunctionalization of aryl sulfoxides via [5,5]-rearrangement

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Listed:
  • Mengjie Hu

    (Zhejiang Normal University
    Dalian University of Technology)

  • Yanping Liu

    (Zhejiang Normal University)

  • Yuchen Liang

    (Zhejiang Normal University)

  • Taotao Dong

    (Zhejiang Normal University)

  • Lichun Kong

    (Zhejiang Normal University)

  • Ming Bao

    (Dalian University of Technology)

  • Zhi-Xiang Wang

    (University of the Chinese Academy of Sciences)

  • Bo Peng

    (Zhejiang Normal University)

Abstract

Aromatic [5,5]-rearrangement can in principle be an ideal protocol to access dearomative compounds. However, the lack of competent [5,5]-rearrangement impedes the advance of the protocol. In this Article, we showcase the power of [5,5]-rearrangement recently developed in our laboratory for constructing an intriguing dearomative sulfonium specie which features versatile and unique reactivities to perform nucleophilic 1,2- and 1,4-addition and cyclization, thus achieving dearomative di- and trifunctionalization of easily accessible aryl sulfoxides. Impressively, the dearomatization products can be readily converted to sulfur-removed cyclohexenones, naphthalenones, bicyclic cyclohexadienones, and multi-substituted benzenes. Mechanistic studies shed light on the key intermediates and the remarkable chemo-, regio- and stereoselectivities of the reactions.

Suggested Citation

  • Mengjie Hu & Yanping Liu & Yuchen Liang & Taotao Dong & Lichun Kong & Ming Bao & Zhi-Xiang Wang & Bo Peng, 2022. "Dearomative di- and trifunctionalization of aryl sulfoxides via [5,5]-rearrangement," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32426-6
    DOI: 10.1038/s41467-022-32426-6
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    References listed on IDEAS

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    1. Harry J. Shrives & José A. Fernández-Salas & Christin Hedtke & Alexander P. Pulis & David J. Procter, 2017. "Regioselective synthesis of C3 alkylated and arylated benzothiophenes," Nature Communications, Nature, vol. 8(1), pages 1-7, April.
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