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Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors

Author

Listed:
  • Shichun Jiang

    (Guizhou University)

  • Wei Wang

    (Guizhou University)

  • Chengli Mou

    (Guizhou University of Traditional Chinese Medicine)

  • Juan Zou

    (Guizhou University of Traditional Chinese Medicine)

  • Zhichao Jin

    (Guizhou University)

  • Gefei Hao

    (Guizhou University)

  • Yonggui Robin Chi

    (Guizhou University
    Nanyang Technological University)

Abstract

The development of suitable electron donors is critical to single-electron-transfer (SET) processes. The use of heteroatom-centered anions as super-electron-donors (SEDs) for direct SET reactions has rarely been studied. Here we show that heteroatom anions can be applied as SEDs to initiate radical reactions for facile synthesis of 3-substituted benzofurans. Phosphines, thiols and anilines bearing different substitution patterns work well in this inter-molecular radical coupling reaction and the 3-functionalized benzofuran products bearing heteroatomic functionalities are given in moderate to excellent yields. The reaction mechanism is elucidated via control experiments and computational methods. The afforded products show promising applications in both organic synthesis and pesticide development.

Suggested Citation

  • Shichun Jiang & Wei Wang & Chengli Mou & Juan Zou & Zhichao Jin & Gefei Hao & Yonggui Robin Chi, 2023. "Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors," Nature Communications, Nature, vol. 14(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-43198-y
    DOI: 10.1038/s41467-023-43198-y
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    References listed on IDEAS

    as
    1. Ya Lv & Guoyong Luo & Qian Liu & Zhichao Jin & Xinglong Zhang & Yonggui Robin Chi, 2022. "Catalytic atroposelective synthesis of axially chiral benzonitriles via chirality control during bond dissociation and CN group formation," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
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