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Divergent functionalization of aldehydes photocatalyzed by neutral eosin Y with sulfone reagents

Author

Listed:
  • Jianming Yan

    (National University of Singapore
    Chongqing Medical University)

  • Haidi Tang

    (National University of Singapore
    National University of Singapore (Suzhou) Research Institute)

  • Eugene Jun Rong Kuek

    (National University of Singapore)

  • Xiangcheng Shi

    (National University of Singapore)

  • Chenguang Liu

    (National University of Singapore)

  • Muliang Zhang

    (National University of Singapore)

  • Jared L. Piper

    (Pfizer Worldwide Research and Development)

  • Shengquan Duan

    (Pfizer Worldwide Research and Development)

  • Jie Wu

    (National University of Singapore
    National University of Singapore (Suzhou) Research Institute)

Abstract

While aldehydes represent a classic class of electrophilic synthons, the corresponding acyl radicals are inherently nucleophilic, which exhibits umpolung reactivity. Generation of acyl radicals typically requires noble metal catalysts or excess oxidants to be added. Herein, we report a convenient and green approach to access acyl radicals, capitalizing on neutral eosin Y-enabled hydrogen atom transfer (HAT) photocatalysis with aldehydes. The generated acyl radicals underwent SOMOphilic substitutions with various functionalized sulfones (X–SO2R’) to deliver value-added acyl products. The merger of eosin Y photocatalysis and sulfone-based SOMOphiles provides a versatile platform for a wide array of aldehydic C–H functionalizations, including fluoromethylthiolation, arylthiolation, alkynylation, alkenylation and azidation. The present protocol features green characteristics, such as being free of metals, harmful oxidants and additives; step-economic; redox-neutral; and amenable to scale-up assisted by continuous-flow technology.

Suggested Citation

  • Jianming Yan & Haidi Tang & Eugene Jun Rong Kuek & Xiangcheng Shi & Chenguang Liu & Muliang Zhang & Jared L. Piper & Shengquan Duan & Jie Wu, 2021. "Divergent functionalization of aldehydes photocatalyzed by neutral eosin Y with sulfone reagents," Nature Communications, Nature, vol. 12(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-27550-8
    DOI: 10.1038/s41467-021-27550-8
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    References listed on IDEAS

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    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.
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    Cited by:

    1. Changha Kim & Yuhyun Kim & Sungwoo Hong, 2024. "1,3-Difunctionalization of [1.1.1]propellane through iron-hydride catalyzed hydropyridylation," Nature Communications, Nature, vol. 15(1), pages 1-10, December.

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