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Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis

Author

Listed:
  • Wei Zhang

    (Sichuan University
    Sichuan University)

  • Zhen Chen

    (Sichuan University)

  • Yuan-Xu Jiang

    (Sichuan University)

  • Li-Li Liao

    (Chongqing University)

  • Wei Wang

    (Sichuan University)

  • Jian-Heng Ye

    (Sichuan University)

  • Da-Gang Yu

    (Sichuan University
    Nankai University)

Abstract

Photocatalytic carboxylation of alkenes with CO2 is a promising and sustainable strategy to synthesize high value-added carboxylic acids. However, it is challenging and rarely investigated for unactivated alkenes due to their low reactivities. Herein, we report a visible-light photoredox-catalyzed arylcarboxylation of unactivated alkenes with CO2, delivering a variety of tetrahydronaphthalen-1-ylacetic acids, indan-1-ylacetic acids, indolin-3-ylacetic acids, chroman-4-ylacetic acids and thiochroman-4-ylacetic acids in moderate-to-good yields. This reaction features high chemo- and regio-selectivities, mild reaction conditions (1 atm, room temperature), broad substrate scope, good functional group compatibility, easy scalability and facile derivatization of products. Mechanistic studies indicate that in situ generation of carbon dioxide radical anion and following radical addition to unactivated alkenes might be involved in the process.

Suggested Citation

  • Wei Zhang & Zhen Chen & Yuan-Xu Jiang & Li-Li Liao & Wei Wang & Jian-Heng Ye & Da-Gang Yu, 2023. "Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-39240-8
    DOI: 10.1038/s41467-023-39240-8
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    References listed on IDEAS

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    1. Qiang Liu & Lipeng Wu & Ralf Jackstell & Matthias Beller, 2015. "Using carbon dioxide as a building block in organic synthesis," Nature Communications, Nature, vol. 6(1), pages 1-15, May.
    2. Yushu Jin & Joaquim Caner & Shintaro Nishikawa & Naoyuki Toriumi & Nobuharu Iwasawa, 2022. "Catalytic direct hydrocarboxylation of styrenes with CO2 and H2," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    3. Qiang Fu & Zhi-Yu Bo & Jian-Heng Ye & Tao Ju & He Huang & Li-Li Liao & Da-Gang Yu, 2019. "Transition metal-free phosphonocarboxylation of alkenes with carbon dioxide via visible-light photoredox catalysis," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
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    Cited by:

    1. Tong Zhang & Jabor Rabeah & Shoubhik Das, 2024. "Red-light-mediated copper-catalyzed photoredox catalysis promotes regioselectivity switch in the difunctionalization of alkenes," Nature Communications, Nature, vol. 15(1), pages 1-10, December.

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