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Intramolecular hydroamination of 2-(2-phenylethynyl)aniline catalyzed by gold nanoparticles

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Abstract

The possibility of using heterogeneous catalysts with a low content of gold in the intramolecular hydroamination of 2-(2-phenylethynyl)aniline was shown. The catalysts with size of gold particles lower than 3 nm exhibit catalytic activity. The study of efficiency of the heterogeneous Au-containing catalysts on different supports (MCM-41, γ-Al2O3(F), NH4 +-Beta, Diasorbamine-60, APTES-MCM-41, and SH-PMO) revealed that the maximum yields of 2-phenylindole were achieved with gold supported on mesoporous silicate materials. A high degree of dispersion of gold in these catalysts is explained by the presence of amino or thiol anchor groups in the support composition. It was found by diffuse reflectance infrared Fourier transform spectroscopy and XPS and XRD methods that gold in these catalysts exists on the support surfaces as small metal particles and due to their size dimensions they show a decreased electron density, i.e., they are electron-deficient Auδ+ nanoparticles.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    E. D. Finashina, O. P. Tkachenko, A. Yu. Startseva, E. A. Redina, V. G. Krasovsky & L. M. Kustov

  2. Department of Chemistry, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119992, Moscow, Russian Federation

    L. M. Kustov & I. P. Beletskaya

Authors
  1. E. D. Finashina
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  2. O. P. Tkachenko
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  3. A. Yu. Startseva
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  4. E. A. Redina
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  5. V. G. Krasovsky
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  6. L. M. Kustov
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  7. I. P. Beletskaya
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Correspondence to E. D. Finashina.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2821—2829, December, 2015.

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Finashina, E.D., Tkachenko, O.P., Startseva, A.Y. et al. Intramolecular hydroamination of 2-(2-phenylethynyl)aniline catalyzed by gold nanoparticles. Russ Chem Bull 64, 2821–2829 (2015). https://doi.org/10.1007/s11172-015-1233-7

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  • DOI: https://doi.org/10.1007/s11172-015-1233-7

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