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Synthesis of piperidines and pyridine from furfural over a surface single-atom alloy Ru1CoNP catalyst

Author

Listed:
  • Haifeng Qi

    (Chinese Academy of Sciences
    Albert-Einstein-Straße 29a)

  • Yurou Li

    (East China University of Science and Technology)

  • Zhitong Zhou

    (Chinese Academy of Sciences)

  • Yueqiang Cao

    (East China University of Science and Technology)

  • Fei Liu

    (Chinese Academy of Sciences)

  • Weixiang Guan

    (Chinese Academy of Sciences)

  • Leilei Zhang

    (Chinese Academy of Sciences)

  • Xiaoyan Liu

    (Chinese Academy of Sciences)

  • Lin Li

    (Chinese Academy of Sciences)

  • Yang Su

    (Chinese Academy of Sciences)

  • Kathrin Junge

    (Albert-Einstein-Straße 29a)

  • Xuezhi Duan

    (East China University of Science and Technology)

  • Matthias Beller

    (Albert-Einstein-Straße 29a)

  • Aiqin Wang

    (Chinese Academy of Sciences
    Chinese Academy of Sciences)

  • Tao Zhang

    (Chinese Academy of Sciences
    Chinese Academy of Sciences)

Abstract

The sustainable production of value-added N-heterocycles from available biomass allows to reduce the reliance on fossil resources and creates possibilities for economically and ecologically improved synthesis of fine and bulk chemicals. Herein, we present a unique Ru1CoNP/HAP surface single-atom alloy (SSAA) catalyst, which enables a new type of transformation from the bio-based platform chemical furfural to give N-heterocyclic piperidine. In the presence of NH3 and H2, the desired product is formed under mild conditions with a yield up to 93%. Kinetic studies show that the formation of piperidine proceeds via a series of reaction steps. Initially, in this cascade process, furfural amination to furfurylamine takes place, followed by hydrogenation to tetrahydrofurfurylamine (THFAM) and then ring rearrangement to piperidine. DFT calculations suggest that the Ru1CoNP SSAA structure facilitates the direct ring opening of THFAM resulting in 5-amino-1-pentanol which is quickly converted to piperidine. The value of the presented catalytic strategy is highlighted by the synthesis of an actual drug, alkylated piperidines, and pyridine.

Suggested Citation

  • Haifeng Qi & Yurou Li & Zhitong Zhou & Yueqiang Cao & Fei Liu & Weixiang Guan & Leilei Zhang & Xiaoyan Liu & Lin Li & Yang Su & Kathrin Junge & Xuezhi Duan & Matthias Beller & Aiqin Wang & Tao Zhang, 2023. "Synthesis of piperidines and pyridine from furfural over a surface single-atom alloy Ru1CoNP catalyst," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
  • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-42043-6
    DOI: 10.1038/s41467-023-42043-6
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    References listed on IDEAS

    as
    1. Xi Zhang & Guoqing Cui & Haisong Feng & Lifang Chen & Hui Wang & Bin Wang & Xin Zhang & Lirong Zheng & Song Hong & Min Wei, 2019. "Platinum–copper single atom alloy catalysts with high performance towards glycerol hydrogenolysis," Nature Communications, Nature, vol. 10(1), pages 1-12, December.
    2. Haifeng Qi & Ji Yang & Fei Liu & LeiLei Zhang & Jingyi Yang & Xiaoyan Liu & Lin Li & Yang Su & Yuefeng Liu & Rui Hao & Aiqin Wang & Tao Zhang, 2021. "Highly selective and robust single-atom catalyst Ru1/NC for reductive amination of aldehydes/ketones," Nature Communications, Nature, vol. 12(1), pages 1-11, December.
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    1. Bin Zhang & Haiyang Yuan & Ye Liu & Zijie Deng & Mark Douthwaite & Nicholas F. Dummer & Richard J. Lewis & Xingwu Liu & Sen Luan & Minghua Dong & Tianjiao Wang & Qingling Xu & Zhijuan Zhao & Huizhen L, 2024. "Ambient-pressure alkoxycarbonylation for sustainable synthesis of ester," Nature Communications, Nature, vol. 15(1), pages 1-13, December.

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