Efficient C{C cross-coupling reactions by (isatin)-Schiff base functionalized magnetic nanoparticle-supported Cu(II) acetate as a magnetically recoverable catalyst

Efficient C{C cross-coupling reactions by (isatin)-Schiff base functionalized magnetic nanoparticle-supported Cu(II) acetate as a magnetically recoverable catalyst

Copper catalysts were simply fabricated through surface modi cation of superparamagnetic iron nanopar- ticles with indoline-2,3-dione(isatin)-Schiff-base and interaction with Cu from low-cost commercially available starting materials.Catalysts were characterized using atomic absorption spectrophotometry, Fourier transform infrared spec- troscopy, X-ray diffraction, thermogravimetric analysis, vibrating sample magnetometry, UV/Vis spectroscopy, scanning electron microscopy, and transmission electron microscopy.These catalysts showed high efficiency for phosphine-free Mizoroki{Heck and Suzuki{Miyaura cross-coupling reactions with good diversity and generality. The catalysts could be easily recovered and reused several times without a signi cant loss in their catalytic activity and stability.

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  • 1. Trzeciak, A. M.; Zio lkowski, J. J. Coord. Chem. Rev. 2005 , 249 , 2308{2322.
  • 2. Farina, V. Adv. Synth. Catal. 2004 , 346 , 1553{1582.
  • 3. Mizutani, T.; Honzawa, S.; Tosaki, S. Y.; Shibasaki, M. Angew. Chem. Int. Ed . 2002 , 41 , 4680{4682.
  • 4. Dez-Gonzalez, S.; Nolan, S. P. Top. Organomet. Chem . 2007 , 21 , 47{82.
  • 5. Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc . 2002 , 124 , 14127{ 14136.
  • 6. Haberli, A.; Leumann, C. J. Org. Lett. 2001 , 3 , 489{492.
  • 7. Makhubela, B. C.; Jardine, A.; Smith, G. S. Appl. Catal. A-Gen. 2011 , 393 , 231{241.
  • 8. Iranpoor, N.; Firouzabadi, H.; Motevalli, S.; Talebi, M. J. Organomet. Chem. 2012 , 708 , 118{124.
  • 9. Yuan, D.; Zhang, Q.; Dou, J. Catal. Commun . 2010 , 11 , 606{610.
  • 10. Costa, N. J.; Kiyohara, P. K.; Monteiro, A. L.; Coppel, Y.; Philippot, K.; Rossi, L. M. J. Catal . 2010 , 76 , 382{389.
  • 11. Mao, J.; Guo, J.; Fang, F.; Ji, S. J. Tetrahedron 2008 , 64 , 3905{3911.
  • 12. Calo, V.; Nacci, A.; Monopoli, A.; Ieva, E.; Cioffi, N. Org. Lett . 2005 , 7 , 617{620.
  • 13. Liu, Y.; Li, D.; Park, C. M. Angew. Che. Int. Ed . 2011 , 50 , 7333{7336.
  • 14. Gigant, N.; Gillaizeau, I. Org. Lett. 2012 , 14 , 3304{3307.
  • 15. Ko, S.; Jang, J. Angew. Chem. Int. Ed . 2006 , 45 , 7564{7567.
  • 16. Cui, J.; He, T.; Zhang, X. Catal. Commun. 2013 , 40 , 66{70.
  • 17. Phan, N. T.; Le, H. V. J. Mol. Catal. A-Chem. 2011 , 334 , 130{138.
  • 18. Zamani, F.; Hosseini, S. M. Catal. Commun . 2014 , 43 , 164{168.
  • 19. Beygzadeh, M.; Alizadeh, A.; Khodaei, M.; Kordestani, D. Catal. Commun . 2013 , 32 , 86{91.
  • 20. Dehghani, F.; Sardarian, A. R.; Esmaeilpour, M. J. Organomet. Chem. 2013 , 743 , 233{240.
  • 21. Taher, A.; Kim, J. B.; Jung, J. Y.; Ahn, W. S.; Jin, M. J. Synlett 2009 , 15 , 2477{2482.
  • 22. Tamizh, M. M.; Karvembu, R. Inorg. Chem. Commun. 2012 , 25 , 30{34.
  • 23. Monier, M.; Ayad, D.; Wei, Y.; Sarhan, A. J. Hazard. Mater. 2010 , 177 , 962{970.
  • 24. Lagasi, M.; Moggi, P. J. Mol. Catal. A-Chem. 2002 , 183 , 61{72.
  • 25. Zhu, M.; Diao, G. J. Phys. Chem. C 2011 , 115 , 24743{24749.
  • 26. Deng, Y.; Qi, D.; Deng, C.; Zhang, X.; Zhao, D. J. Am. Chem. Soc. 2008 , 130 , 28{29.
  • 27. Wang, B.; Wu, X. L.; Shu, C. Y.; Guo, Y. G.; Wang, C. R. J. Mat. Chem . 2010 , 20 , 10661{10664.
  • 28. Qadir, M.; Mochel, T.; Hii, K. K. Tetrahedron 2000 , 56 , 7975{7979.
  • 29. Zhang, M.; Shao, C.; Guo, Z.; Zhang, Z.; Mu, J.; Cao, T.; Liu, Y. ACS Appl. Mater. Interfaces 2011 , 3 , 369{377.
  • 30. Irie, H.; Miura, S.; Kamiya, K.; Hashimoto, K. Chem. Phys. Lett. 2008 , 457 , 202{205.
  • 31. Lee, S. S.; Bai, H.; Liu, Z.; Sun, D. D. Water Res. 2013 , 47 , 4059{4073.
  • 32. Ari n, S. A.; Jalaludin, S.; Djaja, N. F.; Saleh, R. Adv. Mater. Res . 2015, 1112 , 221{227.
  • 33. Bagherzadeh, M.; Ashouri, F.; Hashemi, L.; Morsali, A. Inorg. Chem. Commun . 2014 , 44 , 10{14.
  • 34. Amini, M.; Bagherzadeh, M.; Rostamnia, S. Chin. Chem. Lett . 2013 , 24 , 433{436.
  • 35. Wu, Q.; Wang, L. Synthesis 2008 , 2008 , 2007{2012.
  • 36. Zhang, T. Y.; Allen, M. J. Tetrahedron Lett. 1999 , 40 , 5813{5816.
  • 37. Yang, Y.; Zhou, R.; Zhao, S.; Li, Q.; Zheng, X. J. Mol. Catal. A-Chem. 2003 , 192 , 303{306.
  • 38. Iyer, S.; Thakur, V. V. J. Mol. Catal. A-Chem . 2000 , 157 , 275{278.
  • 39. Thathagar, M. B.; Beckers, J.; Rothenberg, G. J. Am. Chem. Soc. 2002 , 124 , 11858{11859.
  • 40. Shao, L.; Qi, C. Appl. Catal. A-Gen . 2013 , 468 , 26{31.
  • 41. Wang, B.; Yang, P.; Ge, Z. W.; Li, C. P. Inorg. Chem. Commun. 2015 , 61 , 13{15.
  • 42. Heshmatpour, F.; Abazari, R.; Balalaie, S. Tetrahedron 2012 , 68 , 3001{3011.
  • 43. Fodor, A.; Hell, Z.; Pirault-Roy, L. Appl. Catal. A-Gen. 2014 , 484 , 39{50.
  • 44. Kim, S. J.; Oh, S. D.; Lee, S.; Choi, S. H. J. Ind. Eng. Chem. 2008 , 14 , 449{456.
  • 45. Xue, X.; Wang, J.; Mei, L.; Wang, Z.; Qi, K.; Yang, B. Colloid Surface B 2013 , 103 , 107{113.
  • 46. Deng, Z.; Wei, J.; Xue, X.; Wang, J.; Chen, L. J. Porous Mat. 2001 , 8 , 37{42.
  • 47. Jiang, Y.; Jiang, J.; Gao, Q.; Ruan, M.; Yu, H.; Qi, L. Nanotechnology 2008 , 19 , 75714{75720.
  • 48. Kamal, A.; Srinivasulu, V.; Seshadri, B. N.; Markandeya, N.; Alari , A.; Shankaraiah, N. Green Chem. 2012 , 14 , 2513{2522.
  • 49. Gao, Z.; Feng, Y.; Cui, F.; Hua, Z.; Zhou, J.; Zhu, Y.; Shi, J. J. Mol. Catal. A-Chem. 2011 , 336 , 51{57.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

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Resorcinarene-mono-benzimidazolium salts as NHC ligands for Suzuki--Miyaura cross-couplings catalysts

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Feyyaz DURAP, Önder METİN

Efficient C--C cross-coupling reactions by (isatin)-Schiff base functionalized magnetic nanoparticle-supported Cu(II) acetate as a magnetically recoverable catalyst

Seyedeh Simin MIRI, Mehdi KHOOBI, Fatemeh ASHOURI, Farnaz JAFARPOUR, Parviz Rashidi RANJBAR, Abbas SHAFIEE

Contribution of heterobifunctional ligands to transition metal-catalysed C{Ccoupling reactions

Agnes LABANDE, Eric DEYDIER, Eric MANOURY, Jean-Claude DARAN, Catherine AUDIN, Rinaldo POLI

Reactivity of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)-ones in apalladium catalyzed Sonogashira cross-coupling reaction

Malose Jack MPHAHLELE, Felix Adetunji OYEYIOLA

The synthesis, characterization, and catalytic properties of ($\kappa ^{2}-C,N)$-palladacycles with N-heterocyclic carbene-based ancillary ligands

MUHAMMET EMİN GÜNAY, GÜLCAN GENÇAY ÇOĞAŞLIOĞLU, RUKİYE FIRINCI

Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald--Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties

Hasan KÜÇÜKBAY, Ülkü YILMAZ, Kemal YAVUZ, Nesrin BUĞDAY