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Efficient aerobic oxidation of alcohols to aldehydes and ketones using a ruthenium carbonyl complex of a tert-butyl-substituted tetramethylcyclopentadienyl ligand as catalyst

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Abstract

Tert-butyl-substituted tetramethylcyclopentadiene [C5HMe t4 Bu] was reacted with Ru3(CO)12 to prepare [(η5-C5Me t4 Bu)Ru(CO)(μ-CO)]2. The complex was characterized by IR, 1H NMR, 13C NMR, elemental analysis, and single-crystal X-ray diffraction. The complex was investigated as a catalyst in the aerobic oxidation of alcohols to the corresponding aldehydes and ketones in the presence of 2,2’,6,6’-tetramethylpiperidine N-oxide (TEMPO) as co-oxidant. The combination of [(η5-C5Me t4 Bu)Ru(CO)(μ-CO)]2 and TEMPO afforded an efficient catalytic system for the aerobic oxidation of a variety of primary and secondary alcohols, giving the corresponding carbonyl compounds in good-to-excellent yields.

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Acknowledgements

The authors gratefully acknowledge the financial support from the National Natural Science Foundation of China (No. 21372061), the Hebei Natural Science Foundation of China (No. B2017205006), and the Key Research Fund of Hebei Normal University (No. L2017Z02).

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Author notes

  1. Zhiqiang Hao, Xinlong Yan and Zhanwei Li contributed equally to this work.

Authors and Affiliations

  1. The College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang, 050024, China

    Zhiqiang Hao, Xinlong Yan, Zhanwei Li, Ruitao Wu, Zhangang Han, Xuezhong Zheng & Jin Lin

  2. School of Pharmacy, Hebei Medical University, Shijiazhuang, 050017, China

    Zhihong Ma

  3. Hebei College of Industry and Technology, Shijiazhuang, 050091, China

    Suzhen Li

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  1. Zhiqiang Hao
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  2. Xinlong Yan
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  5. Zhihong Ma
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  9. Jin Lin
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Corresponding authors

Correspondence to Zhihong Ma or Jin Lin.

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Hao, Z., Yan, X., Li, Z. et al. Efficient aerobic oxidation of alcohols to aldehydes and ketones using a ruthenium carbonyl complex of a tert-butyl-substituted tetramethylcyclopentadienyl ligand as catalyst. Transit Met Chem 43, 635–640 (2018). https://doi.org/10.1007/s11243-018-0251-3

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  • DOI: https://doi.org/10.1007/s11243-018-0251-3

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