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Cascade cyclization of alkene-tethered acylsilanes and allylic sulfones enabled by unproductive energy transfer photocatalysis

Author

Listed:
  • Yunxiao Zhang

    (Wuhan University
    Wuhan University)

  • Yizhi Zhang

    (Wuhan University)

  • Chen Ye

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Xiaotian Qi

    (Wuhan University)

  • Li-Zhu Wu

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Xiao Shen

    (Wuhan University
    Wuhan University)

Abstract

Developing photo-induced cascade cyclization of alkene-tethered acylsilanes is challenging, because acylsilanes are unstable under light irradiation. Herein, we report that the energy transfer from excited acylsilanes to a photocatalyst that possesses lower triplet energy can inhibit the undesired decomposition of acylsilanes. With neutral Eosin Y as the photocatalyst, an efficient synthesis of cyclopentanol derivatives is achieved with alkene-tethered acylsilanes and allylic sulfones. The reaction shows broad substrate scope and the synthetic potential of this transformation is highlighted by the construction of cyclopentanol derivatives which contain fused-ring or bridged-ring.

Suggested Citation

  • Yunxiao Zhang & Yizhi Zhang & Chen Ye & Xiaotian Qi & Li-Zhu Wu & Xiao Shen, 2022. "Cascade cyclization of alkene-tethered acylsilanes and allylic sulfones enabled by unproductive energy transfer photocatalysis," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-33730-x
    DOI: 10.1038/s41467-022-33730-x
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    References listed on IDEAS

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    1. Benjamin D. Ravetz & Andrew B. Pun & Emily M. Churchill & Daniel N. Congreve & Tomislav Rovis & Luis M. Campos, 2019. "Author Correction: Photoredox catalysis using infrared light via triplet fusion upconversion," Nature, Nature, vol. 570(7759), pages 24-24, June.
    2. Benjamin D. Ravetz & Andrew B. Pun & Emily M. Churchill & Daniel N. Congreve & Tomislav Rovis & Luis M. Campos, 2019. "Photoredox catalysis using infrared light via triplet fusion upconversion," Nature, Nature, vol. 565(7739), pages 343-346, January.
    3. Zhaoliang Yang & Yunhong Niu & Xiaoqian He & Suo Chen & Shanshan Liu & Zhengyu Li & Xiang Chen & Yunxiao Zhang & Yu Lan & Xiao Shen, 2021. "Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    4. Xiang Chen & Xingxing Gong & Zhengyu Li & Gang Zhou & Zhihong Zhu & Weilu Zhang & Shanshan Liu & Xiao Shen, 2020. "Direct transfer of tri- and di-fluoroethanol units enabled by radical activation of organosilicon reagents," Nature Communications, Nature, vol. 11(1), pages 1-9, December.
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