Skip to main content
Log in

Colloidal and Nanosized Catalysts in Organic Synthesis: XXIII. Reductive Amination of Carbonyl Compounds Catalyzed by Nickel Nanoparticles in a Plug-Flow Reactor

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Reductive amination of aldehydes and ketones with primary and secondary amines under catalysis with nickel nanoparticles supported on zeolite X, MgO, or activated carbon in the gas phase or in the gas-liquid system in a plug-flow reactor proceeds at atmospheric pressure of hydrogen with the formation of secondary or tertiary amines in high yield.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Nebykov, D.N., Popov Yu.V., Mokhov, V.M., Latyshova, S.E., Shcherbakova, K.V., Nemtseva, N.V., and Shishkin, E.V., Russ. J. Gen. Chem., 2019, vol. 89, no. 10, p. 1985. https://doi.org/10.1134/S1070363219100013

    Article  CAS  Google Scholar 

  2. Higassio, Y.S. and Shoji, T., Appl. Catal. (A), 2001, vol. 221, nos. 1–2, p. 197. https://doi.org/10.1016/s0926-860x(01)00815-8

    Article  Google Scholar 

  3. Rani, V.R., Srinivas, N., Kulkarni, S.J., and Raghavan, K.V., J. Mol. Catal. (A), 2002, vol. 187, no. 2, p. 237. https://doi.org/10.1016/s1381-1169(02)00208-x

    Article  Google Scholar 

  4. Ward, J. and Wohlgemuth, R., Curr. Org. Chem., 2010, vol. 14, no. 17, p. 1914. https://doi.org/10.2174/138527210792927546

    Article  CAS  Google Scholar 

  5. Nador, F., Moglie, Y., Ciolino, A., Pierini, A., Dorn, V., Yus, M., Alonso, F., and Radivoy, G., Tetrahedron, Lett., 2012, vol. 53, no. 25, p. 3156. https://doi.org/10.1016/j.tetlet.2012.04.054

    Article  CAS  Google Scholar 

  6. Menche, D., Bçhm, S., Li, J., Rudolph, S., and Zander, W., Tetrahedron, Lett., 2007, vol. 48, no. 3, p. 365. https://doi.org/10.1016/j.tetlet.2006.11.082

    Article  CAS  Google Scholar 

  7. Wang, C., Pettman, A., Basca, J., and Xiao, J., Angew. Chem. Int. Ed., 2010, vol. 49, no. 41, p. 7548. https://doi.org/10.1002/anie.201002944

    Article  CAS  Google Scholar 

  8. Jung, Y.J., Bae, J.W., Park, E.S., Chang, Y.M., and Yoon, C.M., Tetrahedron, 2003, vol. 59, no. 51, p. 10331. https://doi.org/10.1016/j.tet.2003.09.054

    Article  CAS  Google Scholar 

  9. Quintin, W.D. and Marcus, E., USA Patent 4190601, 1978.

    Google Scholar 

  10. Pillai, R.B.C., Proc. Indian Nat. Sci. Acad., 1995, vol. 61, no. 2A, p. 97.

    CAS  Google Scholar 

  11. Tararov, V.I., Kadyrov, R., Riermeier, T.H., and Börner, A., Chem. Commun., 2000, no. 19, p. 1867. https://doi.org/10.1039/B005777K

    Google Scholar 

  12. Huang, H., Zhao, Y., Yang, Y., Zhou, L., and Chang, M., Org. Lett., 2017, vol. 19, no. 8, p. 1942. https://doi.org/10.1021/acs.orglett.7b00212

    Article  CAS  Google Scholar 

  13. Li, C., Villa-Marcos, B., and Xiao, J., J. Am. Chem. Soc., 2009, vol. 131, no. 20, p. 6967. https://doi.org/10.1021/ja9021683

    Article  CAS  Google Scholar 

  14. Santoro, F., Psaro, R., Ravasio, N., and Zaccheria, F., ChemCatChem., 2012, vol. 4, no. 9, p. 1249. https://doi.org/10.1002/cctc.201200213

    Article  CAS  Google Scholar 

  15. Pisiewicz, S., Stemmler, T., Surkus A.-E., Junge, K., and Beller, M., ChemCatChem., 2015, vol. 7, no. 1, p. 62. https://doi.org/10.1002/cctc.201402527

    Article  CAS  Google Scholar 

  16. Domine, M.E., Hernández-Soto, M.C., Navarro, M.T., and Pérez, Y., Catalysis Today, 2011, vol. 172, no. 1, p. 13. https://doi.org/10.1016/j.cattod.2011.05.013

    Article  CAS  Google Scholar 

  17. Liu, J., Fitzgeraldand, A.E., and Mani, N.S., Synthesis, 2012, vol. 44, no. 15, p. 2469. https://doi.org/10.1055/s-0032-1316550

    Article  CAS  Google Scholar 

  18. Sharma, S.K., Lynch, J., Sobolewska, A.M., Plucinski, P., Watson, R.J., and Williams, J.J.M., Catal. Sci. Technol., 2013, vol. 3, p. 85. https://doi.org/10.1039/C2CY20431B

    Article  CAS  Google Scholar 

  19. Zotova, N., Roberts, F.J., Kelsall, G.H., Jessiman, A.S., Hellgardt, K., and Hii, K.K., Green Chem., 2012, vol. 14, p. 226. https://doi.org/10.1039/C1GC16118K

    Article  CAS  Google Scholar 

  20. Chieffi, G., Braun, M., and Esposito, D., ChemSusChem., 2015, vol. 8, no. 21, p. 3590. https://doi.org/10.1002/cssc.201500804

    Article  CAS  Google Scholar 

  21. Falus, P., Boros, Z., Hornyanszky, G., Nagy, J., Darvas, F., Urge, L., and Poppe, L., Tetrahedron Lett., 2011, vol. 52, p. 1310. https://doi.org/10.1016/j.tetlet.2011.01.062

    Article  CAS  Google Scholar 

  22. Laroche, B., Ishitani, H., and Kobayashi Sh., Adv. Synth. Catal., 2018, vol. 360, p. 4699. https://doi.org/10.1002/adsc.201801457

    Article  CAS  Google Scholar 

  23. Popov, Yu.V., Mokhov, V.M., Latyshova, S.E., Nebykov, D.N., Panov, A.O., and Davydova, T.M., Russ. J. Gen. Chem., 2018, vol. 88, no. 10, p. 2035. https://doi.org/10.1134/S1070363218100018

    Article  CAS  Google Scholar 

  24. Popov, Yu.V., Mokhov, V.M., Nebykov, D.N., Shcherbakova, K.V., and Dontsova, A.A., Russ. J. Gen. Chem., 2018, vol. 88, no. 1, p. 20. https://doi.org/10.1134/S1070363218010048

    Article  CAS  Google Scholar 

  25. Popov, Yu.V., Mokhov, V.M., Latyshova, S.E., Nebykov, D.N., Panov, A.O., and Pletneva, M.Yu., Russ. J. Gen. Chem., 2017, vol. 87, no. 10, p. 2276. https://doi.org/10.1134/S107036321710005X

    Article  CAS  Google Scholar 

  26. Mokhov, V.M., Popov, Yu.V., and Nebykov, D.N., Russ. J. Gen. Chem., 2014, vol. 84, no. 9, p. 1656. https://doi.org/10.1134/S1070363214090023

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. M. Mokhov.

Ethics declarations

No conflict of interest was declared by the authors.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 12, pp. 1807–1815.

For communication XXII, see [1].

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mokhov, V.M., Popov, Y.V., Paputina, A.N. et al. Colloidal and Nanosized Catalysts in Organic Synthesis: XXIII. Reductive Amination of Carbonyl Compounds Catalyzed by Nickel Nanoparticles in a Plug-Flow Reactor. Russ J Gen Chem 89, 2333–2340 (2019). https://doi.org/10.1134/S1070363219120016

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363219120016

Keywords

Navigation