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Accessing chiral sulfones bearing quaternary carbon stereocenters via photoinduced radical sulfur dioxide insertion and Truce–Smiles rearrangement

Author

Listed:
  • Jiapian Huang

    (Taizhou University)

  • Fei Liu

    (Taizhou University)

  • Ling-Hui Zeng

    (Zhejiang University City College)

  • Shaoyu Li

    (Taizhou University)

  • Zhiyuan Chen

    (Zhejiang University City College)

  • Jie Wu

    (Taizhou University
    Chinese Academy of Sciences
    Henan Normal University)

Abstract

From the viewpoint of synthetic accessibility and functional group compatibility, photoredox-catalyzed sulfur dioxide insertion strategy enables in situ generation of functionalized sulfonyl radicals from easily accessible starting materials under mild conditions, thereby conferring broader application potential. Here we present two complementary photoinduced sulfur dioxide insertion systems to trigger radical asymmetric Truce–Smiles rearrangements for preparing a variety of chiral sulfones that bear a quaternary carbon stereocenter. This protocol features broad substrate scope and excellent stereospecificity. Aside from scalability, the introduction of a quaternary carbon stereocenter at position β to bioactive molecule-derived sulfones further demonstrates the practicality and potential of this methodology.

Suggested Citation

  • Jiapian Huang & Fei Liu & Ling-Hui Zeng & Shaoyu Li & Zhiyuan Chen & Jie Wu, 2022. "Accessing chiral sulfones bearing quaternary carbon stereocenters via photoinduced radical sulfur dioxide insertion and Truce–Smiles rearrangement," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-34836-y
    DOI: 10.1038/s41467-022-34836-y
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    References listed on IDEAS

    as
    1. Shi Cao & Wei Hong & Ziqi Ye & Lei Gong, 2021. "Photocatalytic three-component asymmetric sulfonylation via direct C(sp3)-H functionalization," Nature Communications, Nature, vol. 12(1), pages 1-12, December.
    2. Lei Li & Zhong-Liang Li & Fu-Li Wang & Zhen Guo & Yong-Feng Cheng & Na Wang & Xiao-Wu Dong & Chao Fang & Jingjiang Liu & Chunhui Hou & Bin Tan & Xin-Yuan Liu, 2016. "Radical aryl migration enables diversity-oriented synthesis of structurally diverse medium/macro- or bridged-rings," Nature Communications, Nature, vol. 7(1), pages 1-11, December.
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    Cited by:

    1. Dmitrii Nagornîi & Fabian Raymenants & Nikolaos Kaplaneris & Timothy Noël, 2024. "C(sp3)–H sulfinylation of light hydrocarbons with sulfur dioxide via hydrogen atom transfer photocatalysis in flow," Nature Communications, Nature, vol. 15(1), pages 1-7, December.

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