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Photocatalytic direct borylation of carboxylic acids

Author

Listed:
  • Qiang Wei

    (Peking University)

  • Yuhsuan Lee

    (Chinese Academy of Sciences)

  • Weiqiu Liang

    (Peking University)

  • Xiaolei Chen

    (Lanzhou University)

  • Bo-shuai Mu

    (Peking University)

  • Xi-Yang Cui

    (Peking University)

  • Wangsuo Wu

    (Lanzhou University)

  • Shuming Bai

    (Chinese Academy of Sciences)

  • Zhibo Liu

    (Peking University
    Peking University)

Abstract

The preparation of high value-added boronic acids from cheap and plentiful carboxylic acids is desirable. To date, the decarboxylative borylation of carboxylic acids is generally realized through the extra step synthesized redox-active ester intermediate or in situ generated carboxylic acid covalent derivatives above 150 °C reaction temperature. Here, we report a direct decarboxylative borylation method of carboxylic acids enabled by visible-light catalysis and that does not require any extra stoichiometric additives or synthesis steps. This operationally simple process produces CO2 and proceeds under mild reaction conditions, in terms of high step economy and good functional group compatibility. A guanidine-based biomimetic active decarboxylative mechanism is proposed and rationalized by mechanistic studies. The methodology reported herein should see broad application extending beyond borylation.

Suggested Citation

  • Qiang Wei & Yuhsuan Lee & Weiqiu Liang & Xiaolei Chen & Bo-shuai Mu & Xi-Yang Cui & Wangsuo Wu & Shuming Bai & Zhibo Liu, 2022. "Photocatalytic direct borylation of carboxylic acids," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-34833-1
    DOI: 10.1038/s41467-022-34833-1
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    References listed on IDEAS

    as
    1. Jianbin Li & Chia-Yu Huang & Mohamad Ataya & Rustam Z. Khaliullin & Chao-Jun Li, 2021. "Direct deoxygenative borylation of carboxylic acids," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    2. Gilbert J. Choi & Qilei Zhu & David C. Miller & Carol J. Gu & Robert R. Knowles, 2016. "Catalytic alkylation of remote C–H bonds enabled by proton-coupled electron transfer," Nature, Nature, vol. 539(7628), pages 268-271, November.
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