Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine

Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine

The catalytic activity of 1,3,5-triazine-pentaethylenehexamine (TAPEHA) polymer-supported Pd nanoparticles was investigated in the reduction of nitro arenes to the corresponding amines by NaBH4 or N2 H4 .H2 O. Optimized reaction conditions for both systems were successfully tested on 20 nitroarenes with different characteristics. Considerably high yields (80% 98% in NaBH4 and 85% 98% in N2 H4) were obtained in a short time and at ambient temperature. In addition to these methods being selective against other reducible functionalities such as CN, Br, Cl, and I, the catalyst can be recovered easily and reused more than ten times.

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  • 1. Lawrence, S. A. Amines: Synthesis, Properties and Applications; Cambridge University Press: New York, NY, USA, 2004, pp. 265-305.
  • 2. Mahdavi, H.; Tamami, B. Synt. Comm. 2005, 35, 1121-1127.
  • 3. Ricci, A. Amino Group Chemistry From Synthesis to the Life Science; Wiley-VCH: Weinheim, Germany, 2008, pp. 335-336.
  • 4. Ficker, M.; Petersen, J. F.; Hansen, J. S.; Christensen, J. B. Org. Prep. Proced. Int. 2014, 46, 176-182.
  • 5. Rahman, A.; Jonnalagadda, S. B. Catal. Lett. 2008, 123, 264-268.
  • 6. Davarpanah, J.; Kiasat, A. R. Catal. Commun. 2013, 41, 6-11.
  • 7. Tumma, M.; Srivastava, R. Catal. Commun. 2013, 37, 64-68.
  • 8. Setamdideh, D.; Khezri, B.; Mollapour, M. Orient. J. Chem. 2011, 27, 991- 996.
  • 9. Goksu, H.; Ho, S. F.; Metin, O.; Korkmaz, K.; Garcia, A. M.; Gultekin, M. S.; Sun, S. ACS Catal. 2014, 4, 1777-1782.
  • 10. Goksu, H. New J. Chem. 2015, 39, 8498-8504.
  • 11. Wang, S.; Wang, Z.; Zha, Z. Dalton Transactions 2009, 43, 9363-9373.
  • 12. Serp, P.; Philippot, K. Nanomaterials in Catalysis; Wiley-VCH: Weinheim, Germany, 2008.
  • 13. Astruc, D. Inorg. Chem. 2007, 46, 1884-1894.
  • 14. Karami, K.; Ghasemi, M.; Naeini, N. H. Catal. Commun. 2013, 38, 10-15.
  • 15. Poli, G.; Giambastiani, G.; Heumann, A. Tetrahedron 2000, 56, 5959-5989.
  • 16. Okamoto, K.; Akiyama, R.; Kobayashi, S. Org. Lett. 2004, 6, 1987-1990.
  • 17. Akiyama, R.; Kobayashi, S. Angew. Chem. Int. Ed. 2001, 40, 3469-3471.
  • 18. Smirnov, V. V.; Pr¨ockl, S. S.; Schmidt, A. F.; K¨ohler, K. Arkivoc 2011, 8, 225-241.
  • 19. Tagata, T.; Nishida, M. J. Org. Chem. 2003, 68, 9412-9415.
  • 20. Kitamura, Y.; Sako, S.; Udzu, T.; Tsutsui, A.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Chem. Commun. (Camb) 2007, 47, 5069-5071.
  • 21. Itoh, T.; Danjo, H.; Sasaki, W.; Urita, K.; Bekyarova, E.; Arai, M.; Imamoto, T.; Yudasaka, M.; Iijima, S.; Kanoh, H.; et al. Carbon 2008, 46, 172-175.
  • 22. Yuan, B.; Pan, Y.; Li, Y.; Yin, B.; Jiang, H. Angew. Chem. 2010, 122, 4148-4152.
  • 23. Zengin, M.; Gen¸c, H.; Demirci, T.; Arslan, M.; Kucukislamoglu, M. Tetrahedron Lett. 2011, 52, 2333-2335.
  • 24. Sonmez, F.; Ercan, H.; Genc, H.; Arslan, M.; Zengin, M.; Kucukislamoglu, M. J. Chem. 2013, 2012, 1-4.
  • 25. Genc, H. Catal. Commun. 2015, 67, 64-67.
  • 26. Sayın, M.; Can, M.; Imamoglu, M.; Arslan, M. React. Funct. Polym. 2015, 88, 31-38.
  • 27. Sivrikaya, S.; Cerrahoglu, E.; Imamoglu, M.; Arslan, M. Toxicol. Environl. Chem. 2013, 95, 899-908.
  • 28. Nemamcha, A.; Rehspringer, J. L.; Khatmi, D. J. Phys. Chem. B 2006, 110, 383-387.
  • 29. Jana, N. R.; Wang, Z. L.; Pal, T. Langmuir 2000, 16, 2457-2463.
  • 30. Redon, R.; Rendon-Lara, S. K.; Fernandez-Osorio, A. L.; Ugalde-Saldivar, V. M. Rev. Adv. Mater. Sci. 2011, 27, 31-42.
  • 31. Ornelas, C.; Diallo, A. K.; Ruiz, J.; Astruc, D. Adv. Synth. Catal. 2009, 351, 2147-2154.
  • 32. Rathore, P. S.; Patidar, R.; Shripathic, T.; Thakore, S. Catal. Sci. Technol. 2015, 5, 286-295.
  • 33. Kassis, A. I.; Khawli, L. A. M-aminophenyltrialkylstannane, U.S. Patent 4,977,288 A, Dec 11, 1990.
  • 34. Modvig, A.; Andersen, T. L.; Taaning, R. H.; Lindhardt, A. T.; Skrydstrup T. J. Org. Chem. 2014, 79, 5861-5868.
  • 35. Gkizis, P. L.; Stratakis, M.; Lykakis, I. N. Catal. Commun. 2013, 36, 48-51.
  • 36. Xu H.; Wolf, C.; Chem Commun. 2009, 21, 3035-3037.
  • 37. Ikemoto, T.; Kawamoto, T.; Wada, H.; Ishida, T.; Ito, T; Isogami, Y.; Miyano, Y.; Mizuno, Y.; Tomimatsu, K.; Hamamura, K.; et al. Tetrahedron 2002, 58, 489-493.
  • 38. Dangel, B.; Manchester, J. I.; Sherer, B. 5-6-bicyclic heteroaromatic compounds with antibacterial activity, W.O. Patent 2,009,027,732 A, Mar 5, 2009.
  • 39. Gomtsyan, A.; Bayburt, E. K.; Schmidt, R. G.; Zheng, G. Z.; Perner J. Didomenico, S.; Koenig, J. R.; Turner, S.; Jinkerson, T.; Drizin, I.; et al. Med. Chem. 2005, 48, 744-752.
  • 40. Fujiwara, K.; Ramesh, A.; Maki, T.; Hasegawa, H.; Ueda, K. J. Hazard. Mater. 2007, 146, 39-50.
  • 41. Gurung, M.; Adhikari, B. B.; Alam, S.; Kawakita, H.; Ohto, K.; Inoue, K. Chem. Eng. J. 2013, 228, 405-414.
  • 42. Desforges, A.; Backov, R.; Deleuze, H.; Mondain-Monval, O. Adv. Funct. Mater. 2005, 15, 1689-1695.
  • 43. He, J.; Zhao, J.; Run, Z.; Zheng, S.; Pang, H. Int. J. Electrochem. Sci. 2014, 9, 7351-7358.
  • 44. Li, J.; Wu, Y.; Pan, Y.; Liu, W.; Zhu, Y.; Guo, J. Ceram. Int. 2008, 34, 1539-1542.
  • 45. Wen, H. L.; Yen, F. S. J. Cryst. Growth 2000, 208, 696-708.