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

Yu Zhou, Zhipan Ma, Junjie Tang, Ning Yan (), Yonghua Du, Shibo Xi, Kai Wang, Wei Zhang, Haimeng Wen and Jun Wang ()
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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)

Nature Communications, 2018, vol. 9, issue 1, 1-10

Abstract: 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.

Date: 2018
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DOI: 10.1038/s41467-018-05351-w

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