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Hydroxyl Functionalized Lewis Acidic Ionic Liquid on Silica: An Efficient Catalyst for the C-3 Friedel-Crafts Benzylation of Indoles with Benzyl Alcohols

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Abstract

In this work, a hydroxyl functionalized Lewis acidic ionic liquid on silica is found to be an efficient heterogeneous catalyst for the C-3 Friedel-Crafts benzylation of indoles with different benzyl alcohols as benzylation agents under mild conditions. This catalytic system benefits from simple operation, work-up and reutilization procedures, wide substrate tolerance, low cost, high catalytic activity and excellent chemo-selectivity. The hybrid combination of hydroxyl functionalized ionic liquid and silica through the formation of hydrogen bond endows this catalyst with high stability in the Friedel-Crafts reaction system, and the catalyst could be easily recycled and reutilized.

Graphical Abstract

A hydroxyl functionalized Lewis acid ionic liquid supported on silica was found to be an efficient catalyst for the C-3 Friedel-Crafts benzylation reaction of iodole with alcohols. This catalyst benefits from low cost, feasible preparation and reutilization, high catalytic activity and selectivity, and the operation and work-up procedures are very simple.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21373079) and Program for Science & Technology Innovation Talents in Universities of Henan Province (14HASTIT015).

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Authors and Affiliations

  1. Key Laboratory of Green Chemical Media and Reactions, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Ministry of Education, Henan Normal University, Xinxiang, 453007, Henan, People’s Republic of China

    Anlian Zhu, Wanlu Feng, Lingjun Li, Qianqian Li & Jianji Wang

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  1. Anlian Zhu
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  2. Wanlu Feng
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  3. Lingjun Li
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  4. Qianqian Li
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  5. Jianji Wang
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Corresponding author

Correspondence to Jianji Wang.

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Zhu, A., Feng, W., Li, L. et al. Hydroxyl Functionalized Lewis Acidic Ionic Liquid on Silica: An Efficient Catalyst for the C-3 Friedel-Crafts Benzylation of Indoles with Benzyl Alcohols. Catal Lett 147, 261–268 (2017). https://doi.org/10.1007/s10562-016-1918-z

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  • DOI: https://doi.org/10.1007/s10562-016-1918-z

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