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One-Pot Myrtenol Amination over Au, Au–Pd and Pd Nanoparticles Supported on Alumina

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Abstract

One-pot bio-based myrtenol amination was studied in the presence of alumina supported Au, Au–Pd and Pd nanoparticles subjected to the thermal treatment under oxidizing or reducing atmosphere. Myrtenol amination with aniline was carried out under nitrogen atmosphere (9 bar) at 453 K using toluene as a solvent. The effect of the active metal along with the influence of redox pre-treatment on the catalytic behavior in the hydrogen borrowing reaction was explored. The catalyst characterization was done by transmission electron microscopy, X-ray photoelectron spectroscopy, inductively coupled plasma optical emission spectroscopy, nitrogen adsorption. The active metal and the catalysts redox pretreatment affected more noticeably selectivity to the reaction products rather than myrtenol conversion. Monometallic Au/Al2O3 catalyst promoted predominantly formation of the target secondary amine and the corresponding imine without a significant impact of the side reaction of C=C bond hydrogenation in myrtenol, whereas monometallic Pd catalyst activated C=C bond resulting in its hydrogenation. At the same time in the presence of Au–Pd simultaneous hydrogenation of both C=C and C=N bond occurred. Au–Pd catalysts activated in oxygen and hydrogen showed different catalytic activity determined by the composition of surface active sites. Monometallic gold catalyst was more effective in the hydrogen transfer in the case of substrates with competitive unsaturated functional groups.

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Acknowledgements

The authors acknowledge the technical assistance of E. Smolentseva, E. Flores, P. Casillas, F. Ruiz, E. Aparicio and J. Peralta. This work was supported by Ministry of Science and Higher Education of the Russian Federation (Project AAAA-A17-117041710075-0).

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Authors and Affiliations

  1. Boreskov Institute of Catalysis, pr. Lavrentieva, 5, Novosibirsk, Russia, 630090

    Yu. S. Demidova & I. L. Simakova

  2. Novosibirsk State University, Pirogova, 2, Novosibirsk, Russia, 630090

    Yu. S. Demidova, I. L. Simakova, K. P. Volcho & N. F. Salakhutdinov

  3. Centro de Nanociencias y Nanotecnología, Universidad Nacional Autónoma de México, km. 107 carretera Tijuana a Ensenada, C.P. 22860, Ensenada, Baja California, Mexico

    M. Estrada & A. Simakov

  4. Bernal Institute, University of Limerick, Limerick, V94 T9PX, Ireland

    S. Beloshapkin

  5. Novosibirsk Institute of Organic Chemistry, pr. Lavrentieva, 9, Novosibirsk, Russia, 630090

    E. V. Suslov, K. P. Volcho & N. F. Salakhutdinov

  6. Process Chemistry Centre, Åbo Akademi University, 20500, Turku/Åbo, Finland

    D. Yu. Murzin

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  1. Yu. S. Demidova
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  2. I. L. Simakova
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  4. S. Beloshapkin
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  7. N. F. Salakhutdinov
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  9. D. Yu. Murzin
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Correspondence to I. L. Simakova.

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Demidova, Y.S., Simakova, I.L., Estrada, M. et al. One-Pot Myrtenol Amination over Au, Au–Pd and Pd Nanoparticles Supported on Alumina. Catal Lett 149, 3454–3464 (2019). https://doi.org/10.1007/s10562-019-02958-6

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  • DOI: https://doi.org/10.1007/s10562-019-02958-6

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