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Catalytic direct hydrocarboxylation of styrenes with CO2 and H2

Author

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  • Yushu Jin

    (Tokyo Institute of Technology, O-okayama, Meguro-ku)

  • Joaquim Caner

    (Tokyo Institute of Technology, O-okayama, Meguro-ku)

  • Shintaro Nishikawa

    (Tokyo Institute of Technology, O-okayama, Meguro-ku)

  • Naoyuki Toriumi

    (Tokyo Institute of Technology, O-okayama, Meguro-ku)

  • Nobuharu Iwasawa

    (Tokyo Institute of Technology, O-okayama, Meguro-ku)

Abstract

A three-component hydrocarboxylation of an olefin with CO2 and H2 could be regarded as a dream reaction, since it would provide a straightforward approach for the synthesis of aliphatic carboxylic acids in perfect atom economy. However, this transformation has not been realized in a direct manner under mild conditions, because boosting the carboxylation with thermodynamically stable CO2 while suppressing the rapid hydrogenation of olefin remains a challenging task. Here, we report a rhodium-catalysed reductive hydrocarboxylation of styrene derivatives with CO2 and H2 under mild conditions, in which H2 served as the terminal reductant. In this approach, the carboxylation process was largely accelerated by visible light irradiation, which was proved both experimentally and by computational studies. Hydrocarboxylation of various kinds of styrene derivatives was achieved in good yields without additional base under ambient pressure of CO2/H2 at room temperature. Mechanistic investigations revealed that use of a cationic rhodium complex was critical to achieve high hydrocarboxylation selectivity.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-35293-3
    DOI: 10.1038/s41467-022-35293-3
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    References listed on IDEAS

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    1. Lipeng Wu & Qiang Liu & Ivana Fleischer & Ralf Jackstell & Matthias Beller, 2014. "Ruthenium-catalysed alkoxycarbonylation of alkenes with carbon dioxide," Nature Communications, Nature, vol. 5(1), pages 1-6, May.
    2. 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.
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    Cited by:

    1. 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.

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