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Immediate hydroxylation of arenes to phenols via V-containing all-silica ZSM-22 zeolite triggered non-radical mechanism

Author

Listed:
  • Yu Zhou

    (Nanjing Tech University (former Nanjing University of Technology))

  • Zhipan Ma

    (Nanjing Tech University (former Nanjing University of Technology))

  • Junjie Tang

    (Nanjing Tech University (former Nanjing University of Technology))

  • Ning Yan

    (National University of Singapore)

  • Yonghua Du

    (Institute of Chemical and Engineering Sciences)

  • Shibo Xi

    (Institute of Chemical and Engineering Sciences)

  • Kai Wang

    (Nanjing Tech University (former Nanjing University of Technology))

  • Wei Zhang

    (Nanjing Tech University (former Nanjing University of Technology))

  • Haimeng Wen

    (Nanjing Tech University (former Nanjing University of Technology))

  • Jun Wang

    (Nanjing Tech University (former Nanjing University of Technology))

Abstract

Hydroxylation of arenes via activation of aromatic Csp2–H bond has attracted great attention for decades but remains a huge challenge. Herein, we achieve the ring hydroxylation of various arenes with stoichiometric hydrogen peroxide (H2O2) into the corresponding phenols on a robust heterogeneous catalyst series of V–Si–ZSM-22 (TON type vanadium silicalite zeolites) that is straightforward synthesized from an unusual ionic liquid involved dry-gel-conversion route. For benzene hydroxylation, the phenol yield is 30.8% (selectivity >99%). Ring hydroxylation of mono-/di-alkylbenzenes and halogenated aromatic hydrocarbons cause the yields up to 26.2% and selectivities above 90%. The reaction is completed within 30 s, the fastest occasion so far, resulting in ultra-high turnover frequencies (TOFs). Systematic characterization including 51V NMR and X-ray absorption fine structure (XAFS) analyses suggest that such high activity associates with the unique non-radical hydroxylation mechanism arising from the in situ created diperoxo V(IV) state.

Suggested Citation

  • Yu Zhou & Zhipan Ma & Junjie Tang & Ning Yan & Yonghua Du & Shibo Xi & Kai Wang & Wei Zhang & Haimeng Wen & Jun Wang, 2018. "Immediate hydroxylation of arenes to phenols via V-containing all-silica ZSM-22 zeolite triggered non-radical mechanism," Nature Communications, Nature, vol. 9(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-05351-w
    DOI: 10.1038/s41467-018-05351-w
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    Cited by:

    1. Ting Zhang & Zhe Sun & Shiyan Li & Baojun Wang & Yuefeng Liu & Riguang Zhang & Zhongkui Zhao, 2022. "Regulating electron configuration of single Cu sites via unsaturated N,O-coordination for selective oxidation of benzene," Nature Communications, Nature, vol. 13(1), pages 1-8, December.

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