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Green Chemistry
Page 5 of 7
Green Chemistry
COMMUNICATION
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4% to 1,2,3,4-tetrahydrocarbazole with 33% yield. In contrast 7. M. T. Kessler, C. Gedig, S. Sahler, P. Wand, S. Robke and M.
DOI: 10.1039/C7GC00513J
to quinoline no favoured hydrogenation of the heteroaromatic
H. G. Prechtl, Catal Sci Technol, 2013, 3, 992-1001.
moiety was obtained using Ru-NPs in [C C (EG)IM]NTf . The 8. H. Konnerth and M. H. G. Prechtl, Chem Commun, 2016, 52
,
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substrates indole and carbazole are not basic like quinoline
9129-9132.
and thus no formation of hydrogen bonds between a Lewis 9. T. N. Gieshoff, A. Welther, M. T. Kessler, M. H. G. Prechtl and
26,
basic substrate and the hydroxyl groups of the IL are formed.
A. J. von Wangelin, Chem Commun, 2014, 50, 2261-2264.
Nevertheless, depending on the used substrate, high 10. M. T. Kessler, S. Robke, S. Sahler and M. H. G. Prechtl, Catal
selectivity for either a single hydrogenated ring or fully Sci Technol, 2014, , 102-108.
hydrogenated ring can be achieved using a simple and active 11. M. T. Kessler, M. K. Hentschel, C. Heinrichs, S. Roitsch and M.
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catalyst system of Ru-NPs dispersed in imidazolium based ILs.
H. G. Prechtl, Rsc Adv, 2014,
2. M. Scott, P. J. Deuss, J. G. de Vries, M. H. G. Prechtl and K.
Barta, Catal Sci Technol, 2016, , 1882-1891.
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Conclusions
To conclude, we developed a practicable catalyst system of Ru-
NPs dispersed in imidazolium based ILs for hydrogenation
reactions of N-heterocyclic compounds including pyrimide,
pyrimidine, pyrrole, pyrrazole substructures. Especially highly
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selective hydrogenation of quinoline to THQ was achieved
6. M. M. Dell'Anna, V. F. Capodiferro, M. Mali, D. Manno, P.
Cotugno, A. Monopoli and P. Mastrorilli, Appl Catal a-Gen,
using a diol-functionalised IL. This transformation is induced by
the formation of hydrogen bonds between the Lewis basic
substrate and the hydroxyl groups of the IL, confirmed by FT-IR
measurements. Moreover good recyclability with high
selectivity provides a relevant catalyst system for possible
future application.
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014, 481, 89-95.
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Acknowledgements
We gratefully acknowledge for financial support the
Ministerium für Innovation, Wissenschaft und Forschung
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23.
1. A. Karakulina, A. Gopakumar, I. Akcok, B. L. Roulier, T.
LaGrange, S. A. Katsyuba, S. Das and P. J. Dyson, Angew
Chem Int Edit, 2016, 55, 292-296.
(
NRW-returnee award 2009 for M. H. G. Prechtl), the
Heisenberg-program (Deutsche Forschungsgemeinschaft), the
Ernst-Haage Foundation (Max-Planck Institute for Chemical
Energy Conversion) for the Ernst-Haage-Prize 2014, the
Alexander-von-Humboldt Foundation (Connect program) and
H. Konnerth acknowledges the Jürgen Manchot Stiftung for a
research scholarship. S. Roitsch is acknowledged for TEM
analysis.
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