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Selective hydrodeoxygenation of α, β-unsaturated carbonyl compounds to alkenes

Author

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  • Tianjiao Wang

    (CAS Key Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Yu Xin

    (CAS Key Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Bingfeng Chen

    (CAS Key Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences)

  • Bin Zhang

    (CAS Key Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences)

  • Sen Luan

    (CAS Key Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Minghua Dong

    (CAS Key Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Yuxuan Wu

    (CAS Key Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Xiaomeng Cheng

    (CAS Key Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Ye Liu

    (CAS Key Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences)

  • Huizhen Liu

    (CAS Key Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Buxing Han

    (CAS Key Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

Abstract

Achieving selective hydrodeoxygenation of α, β-unsaturated carbonyl groups to alkenes poses a substantial challenge due to the presence of multiple functional groups. In this study, we develop a ZnNC-X catalyst (X represents the calcination temperature) that incorporates both Lewis acidic-basic sites and Zn-Nx sites to address this challenge. Among the catalyst variants, ZnNC-900 catalyst exhibits impressive selectivity for alkenes in the hydrodeoxygenation of α, β-unsaturated carbonyl compounds, achieving up to 94.8% selectivity. Through comprehensive mechanism investigations and catalyst characterization, we identify the Lewis acidic-basic sites as responsible for the selective hydrogenation of C=O bonds, while the Zn-Nx sites facilitate the subsequent selective hydrodeoxygenation step. Furthermore, ZnNC-900 catalyst displays broad applicability across a diverse range of unsaturated carbonyl compounds. These findings not only offer valuable insights into the design of effective catalysts for controlling alkene selectivity but also extend the scope of sustainable transformations in synthetic chemistry.

Suggested Citation

  • Tianjiao Wang & Yu Xin & Bingfeng Chen & Bin Zhang & Sen Luan & Minghua Dong & Yuxuan Wu & Xiaomeng Cheng & Ye Liu & Huizhen Liu & Buxing Han, 2024. "Selective hydrodeoxygenation of α, β-unsaturated carbonyl compounds to alkenes," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-46383-9
    DOI: 10.1038/s41467-024-46383-9
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    References listed on IDEAS

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    1. Shulin Liu & Minghua Dong & Yuxuan Wu & Sen Luan & Yu Xin & Juan Du & Shaopeng Li & Huizhen Liu & Buxing Han, 2022. "Solid surface frustrated Lewis pair constructed on layered AlOOH for hydrogenation reaction," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    2. Chao Xie & Longfei Lin & Liang Huang & Zixin Wang & Zhiwei Jiang & Zehui Zhang & Buxing Han, 2021. "Zn-Nx sites on N-doped carbon for aerobic oxidative cleavage and esterification of C(CO)-C bonds," Nature Communications, Nature, vol. 12(1), pages 1-12, December.
    3. Jiankang Zhang & Zhe Gao & Sen Wang & Guofu Wang & Xiaofeng Gao & Baiyan Zhang & Shuangfeng Xing & Shichao Zhao & Yong Qin, 2019. "Origin of synergistic effects in bicomponent cobalt oxide-platinum catalysts for selective hydrogenation reaction," Nature Communications, Nature, vol. 10(1), pages 1-8, December.
    4. Houbing Zou & Jinyu Dai & Jinquan Suo & Rammile Ettelaie & Yuan Li & Nan Xue & Runwei Wang & Hengquan Yang, 2021. "Dual metal nanoparticles within multicompartmentalized mesoporous organosilicas for efficient sequential hydrogenation," Nature Communications, Nature, vol. 12(1), pages 1-11, December.
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