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Supported Au/MIL-53(Al): a reusable green solid catalyst for the three-component coupling reaction of aldehyde, alkyne, and amine

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Abstract

MIL-53(Al) was synthesized in a mixture of aluminum nitrate, 1,4-benzenedicarboxylic acid, and water using the hydrothermal and reflux methods. A metal–organic-framework-supported Au-based heterogeneous catalyst (Au/MIL-53(Al)) was prepared using the impregnation method under mild conditions with HAuCl4·4H2O as the Au precursors. The physicochemical properties of the samples were characterized by X-ray diffraction (XRD), infrared spectroscopy (IR), X-ray photoelectron spectroscopy (XPS), thermogravimetric analysis (TG), transmission electron microscopy (TEM), and inductively coupled plasma atomic emission spectroscopy (ICP–AES). MIL-53(Al) indicates excellent chemical stability without structure degradation during the loading and catalysis process. The XPS spectra indicate that the catalyst Au/MIL-53(Al) contains coexisting Au0 and Au3+ ions. The catalytic performance of the catalyst was examined in one-pot synthesis of structurally divergent propargylamines via three component coupling of aldehyde, alkyne, and amine (A3) in 1,4-dioxane. The results showed that the catalyst Au/MIL-53(Al) displayed high activity without any additives or an inert atmosphere (the yield reached 97.9 % for 5 h at 120 °C). Au/MIL-53(Al) has proven to be applicable to a wide range of substrates. Various aromatic/aliphatic aldehydes, aromatic alkynes, and piperidine were able to undergo A3 coupling on the catalyst Au/MIL-53(Al). In addition, the catalyst could be recovered easily by centrifugation and reused three times.

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Acknowledgments

This work was supported by the Promotive Research Fund for Young and Middle-aged Scientists of Shandong Province (BS2014CL021, BS2015CL012), the National Natural Science Foundation of Shandong (ZR2014BL003, ZR2015BM005), the Project of Shandong Province Higher Educational Science and Technology Program (J14LC01, J15LA09), and the Technology Research and Development Program of Weifang (201301035, 2015GX003).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering and Environmental Engineering, Weifang University, Weifang, 261061, Shandong, China

    Lili Liu, Xishi Tai, Nana Zhang, Qingguo Meng & Chunling Xin

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  1. Lili Liu
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  2. Xishi Tai
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  3. Nana Zhang
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  4. Qingguo Meng
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Correspondence to Xishi Tai.

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Liu, L., Tai, X., Zhang, N. et al. Supported Au/MIL-53(Al): a reusable green solid catalyst for the three-component coupling reaction of aldehyde, alkyne, and amine. Reac Kinet Mech Cat 119, 335–348 (2016). https://doi.org/10.1007/s11144-016-1034-5

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