Colloidal and nanosized catalysts in organic synthesis: XXV. Reductive alkylation of nitroarenes with alcohols in the presence of a supported copper nanocatalyst

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

Using a modified deposition-precipitation method followed by sodium borohydride reduction of the precursor deposited on γ-Al2O3, copper-containing catalysts were obtained, which allow the continuous process of reductive alkylation of nitroarenes with alkanols at 200-220°C and atmospheric pressure of hydrogen with mono- N -alkylated products selectivity up to 100% and complete conversion of nitroarenes.

About the authors

D. N Nebykov

Volgograd State Technical University

Email: nervwho@gmail.com

A. V Razvalyaeva

Volgograd State Technical University

A. O Panov

Volgograd State Technical University

S. E Latyshova

Volgograd State Technical University

V. M Mokhov

Volgograd State Technical University

References

  1. Попов Ю.В., Мохов В.М., Небыков Д.Н., Ширханян П.М., Гендлер Т.А., Шемет В.В. // ЖОХ. 2020. Т. 90. Вып. 6. С. 823
  2. Popov Yu.V., Mokhov V.M., Nebykov D.N., Shirkhanyan P.M., Gendler T.A., Shemet V.V. // Russ. J. Gen. Chem. 2020. Vol. 90. N 6. P. 931. doi: 10.31857/S0044460X20060013
  3. Dell'Anna M.M., Mastrorilli P., Rizzuti A., Leonelli C. // Appl. Catal. (A). 2011. Vol. 401. N 1-2. P. 134. doi: 10.1016/j.apcata.2011.05.010
  4. Artiukha E.A., Nuzhdin A.L., Bukhtiyarova G.A., Zaytsev S.Y., Plyusnin P.E., Shubin Y.V., Bukhtiyarov V.I. // Catal. Sci. Technol. 2015. Vol. 5. N 10. Р. 4741. doi: 10.1039/c5cy00964b
  5. Chabukswar V.V., Bhavsar S.V., Horne A.S., Handore K., Gaikwad V.B., Mohite K.C. // Macromol. Symp. 2013. Vol. 327. N 1. P. 39. doi: 10.1002/masy.201350504
  6. Cui X., Zhang Y., Shi, F., Deng Y. // Chem. Eur. J. 2011. Vol. 17. N 9. P. 2587. doi: 10.1002/chem.201003095
  7. Lee C.-C., Liu S.-T. // ChemComm. 2011. Vol. 47. N 24. Р. 6981. doi: 10.1039/C1CC11609F
  8. Peng Q., Zhang Y., Shi F., Deng Y. // ChemComm. 2011. Vol. 47. N 22. Р. 6476. doi: 10.1039/c1cc11057h
  9. Stíbal D., Sá, J., van Bokhoven J.A. // Catal. Sci. Technol. 2013. Vol. 3. N 1. Р. 94. doi: 10.1039/c2cy20511d
  10. Selvam K., Sakamoto H., Shiraishi Y., Hirai T. // New J. Chem. 2015. Vol. 39 N 4. P. 2467. doi: 10.1039/c4nj01851f
  11. Shuvalova E.V., Kirichenko O.A. // Mendeleev Commun. 2021. Vol. 31. N 6. P. 875. doi: 10.1016/j.mencom.2021.11.036
  12. Kour G., Gupta M., Thirunavukkarasu B.V.K. // New J. Chem. 2016. Vol. 40 N 10. Р. 8535. doi: 10.1039/c6nj01464j
  13. Ye T-N., Lu Y., Li J., Nakao T., Yang H., Tada T., Kitano M., Hosono H. // J. Am. Chem. Soc. 2017. Vol. 139. N 47 Р. 17089. doi: 10.1021/jacs.7b08252
  14. Song G., Tian J., Chen L., Li Y. // Res. Chem. Intermed. 2014. Vol. 41. N 8. P. 5399. doi: 10.1007/s11164-014-1641-6
  15. Nuzhdin A.L., Artiukha E.A., Bukhtiyarova G.A., Derevyannikova E.A., Bukhtiyarov V.I. // Catal. Commun. 2017. Vol. 102. P. 108. doi: 10.1016/j.catcom.2017.09.001.
  16. Мохов В.М., Попов Ю.В., Небыков Д.Н., Нищик Е.В., Щербакова К.В., Зотов Ю.Л. // ЖОХ. 2019. Т. 89. Вып. 8. C. 1151
  17. Mokhov V.M., Popov Yu.V., Nebykov D.N., Nishchik Ye.V., Shcherbakova K.V., Zotov Yu.L. // Russ. J. Gen. Chem. 2019. Vol. 89. N 8. P. 1549. doi: 10.1134/S1070363219080012
  18. Мохов В.М., Попов Ю.В., Папутина А.Н., Небыков Д.Н., Шишкин Е.В. // ЖОХ. 2019. Т. 89. Вып. 12. C. 1807
  19. Mokhov V.M., Popov Yu.V., Paputina A.N., Nebykov D.N., Shishkin Ye.V. // Russ. J. Gen. Chem. 2019. Vol. 89. N 12. P. 2333. doi: 10.1134/S1070363219120016
  20. Попов Ю.В., Мохов В.М., Латышова С.Е., Панов А.О., Ширханян П.М. // ЖОХ. 2017. Т. 87. Вып. 11. C. 1804
  21. Popov Yu.V., Mokhov V.M., Latyshova S.E., Panov A.O., Shirkhanyan P.M. // Russ. J. Gen. Chem. 2017. Vol. 87. N 11. P. 2546. doi: 10.1134/S1070363217110068
  22. He Z., Lin H., He P., Yuan Y. // J. Catal. 2011. Vol. 277. Р. 54. doi: 10.1016/j.jcat.2010.10.010
  23. Villagran-Olivares A.C., Gomez M.F., Lopez C., Barroso M.N., Abello M.C. // Appl. Catal. (B). 2019. Vol. 264. N 5. P. 118510. doi: 10.1016/j.apcatb.2019.118510
  24. Badoga S., Mouli K.C., Soni K.K., Dalai A.K., Adjaye J. // Appl. Catal. (B). 2012. Vol. 125 Р. 67. doi: 10.1016/j.apcatb.2012.05.015

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2023 Russian Academy of Sciences