Yıl: 2017 Cilt: 41 Sayı: 5 Sayfa Aralığı: 784 - 792 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

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

Öz:
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.
Anahtar Kelime:

Konular: Mühendislik, Kimya
Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • 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.
APA GENÇ H, Zengin M, KÜÇÜKİSLAMOĞLU M, Imamoglu M, TOPLAN H, Arslan M (2017). Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine. , 784 - 792.
Chicago GENÇ HAYRİYE,Zengin Mustafa,KÜÇÜKİSLAMOĞLU MUSTAFA,Imamoglu Mustafa,TOPLAN HÜSEYİN ÖZKAN,Arslan Mustafa Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine. (2017): 784 - 792.
MLA GENÇ HAYRİYE,Zengin Mustafa,KÜÇÜKİSLAMOĞLU MUSTAFA,Imamoglu Mustafa,TOPLAN HÜSEYİN ÖZKAN,Arslan Mustafa Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine. , 2017, ss.784 - 792.
AMA GENÇ H,Zengin M,KÜÇÜKİSLAMOĞLU M,Imamoglu M,TOPLAN H,Arslan M Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine. . 2017; 784 - 792.
Vancouver GENÇ H,Zengin M,KÜÇÜKİSLAMOĞLU M,Imamoglu M,TOPLAN H,Arslan M Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine. . 2017; 784 - 792.
IEEE GENÇ H,Zengin M,KÜÇÜKİSLAMOĞLU M,Imamoglu M,TOPLAN H,Arslan M "Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine." , ss.784 - 792, 2017.
ISNAD GENÇ, HAYRİYE vd. "Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine". (2017), 784-792.
APA GENÇ H, Zengin M, KÜÇÜKİSLAMOĞLU M, Imamoglu M, TOPLAN H, Arslan M (2017). Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine. Turkish Journal of Chemistry, 41(5), 784 - 792.
Chicago GENÇ HAYRİYE,Zengin Mustafa,KÜÇÜKİSLAMOĞLU MUSTAFA,Imamoglu Mustafa,TOPLAN HÜSEYİN ÖZKAN,Arslan Mustafa Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine. Turkish Journal of Chemistry 41, no.5 (2017): 784 - 792.
MLA GENÇ HAYRİYE,Zengin Mustafa,KÜÇÜKİSLAMOĞLU MUSTAFA,Imamoglu Mustafa,TOPLAN HÜSEYİN ÖZKAN,Arslan Mustafa Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine. Turkish Journal of Chemistry, vol.41, no.5, 2017, ss.784 - 792.
AMA GENÇ H,Zengin M,KÜÇÜKİSLAMOĞLU M,Imamoglu M,TOPLAN H,Arslan M Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine. Turkish Journal of Chemistry. 2017; 41(5): 784 - 792.
Vancouver GENÇ H,Zengin M,KÜÇÜKİSLAMOĞLU M,Imamoglu M,TOPLAN H,Arslan M Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine. Turkish Journal of Chemistry. 2017; 41(5): 784 - 792.
IEEE GENÇ H,Zengin M,KÜÇÜKİSLAMOĞLU M,Imamoglu M,TOPLAN H,Arslan M "Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine." Turkish Journal of Chemistry, 41, ss.784 - 792, 2017.
ISNAD GENÇ, HAYRİYE vd. "Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine". Turkish Journal of Chemistry 41/5 (2017), 784-792.