Substituted 2-(2'-pyridyl)benzimidazole palladium(II) complexes as an efficient catalytic system for Suzuki{Miyaura cross-coupling reactions

Substituted 2-(2'-pyridyl)benzimidazole palladium(II) complexes as an efficient catalytic system for Suzuki{Miyaura cross-coupling reactions

A new series of N;N -type 2-(2'-pyridyl)benzimidazole ligands ( 2A 1 , 2A 2 , 3B 1 , 3B 2 , 3B 3 , and 4C 1 ) and their Pd(II) complexes ( 5A 1 , 5A 2 , 6B 1 , 6B 2 , 6B 3 , and 7C 1 ) were prepared and characterized by conventional spectroscopic methods and elemental analyses. The incorporation of N -coordinated benzimidazole complexes of palla- dium gave high catalytic activity in the Suzuki{Miyaura coupling of aryl halides substrates. After determining the best active catalyst as 5A 1 , bearing the mesityl substituent on the benzimidazole ring with the Pd(II) ion, optimization studies were carried out via changing the substrate, base, time, atmosphere, and the effect of water. The DMF:H 2 O (4/1) and Cs 2 CO 3 as base were found to be critical for the efficiency of the reaction yield (100%).

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  • 1. Tsuji, J. Palladium Reagents and Catalysts ; Wiley: Chichester, UK, 1995.
  • 2. Weskamp, T.; Bohm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 1999 , 585 , 348{352.
  • 3. Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979 , 20 , 3437{3440.
  • 4. Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001 , 123 , 2719{2724.
  • 5. Herrmann, W. A.; Bohm, V. P. W.; Reisinger, C. J. Organomet. Chem. 1999 , 576 , 23{41.
  • 6. Lee, H. M.; Nolan, S. P. Org. Lett. 2000 , 2 , 2053{2055.
  • 7. Stille, J. K. Angew. Chem. Int. Ed. Engl. 1986 , 25 , 508{524.
  • 8. Miyaruna, N.; Suzuki, A. Chem. Rev. 1995 , 95 , 2457{2483.
  • 9. Suzuki, A. J. Organomet. Chem. 1999 , 576 , 147{168.
  • 10. Stanforth, S. P. Tetrahedron 1998 , 54 , 263{303.
  • 11. Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001 , 57 , 7449{7476.
  • 12. Crisp, G. T. Chem. Soc. Rev. 1998 , 27 , 427{436.
  • 13. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002 , 58 , 9633{9695.
  • 14. Uozumi, Y. Top. Curr. Chem. 2004 , 242 , 77{112.
  • 15. Torborg, C.; Beller, M. Adv. Synth. Catal. 2009 , 351 , 3027{3043.
  • 16. Magano, J.; Dunetz, J. R. Chem. Rev. 2011 , 111 , 2177{2250.
  • 17. Picquet, M. Platin. Met. Rev. 2013 , 57 , 272{280.
  • 18. Miyaura, N.; Suzuki, A. Chem. Rev. 1995 , 95 , 2457{2483.
  • 19. Suzuki, A. J. Organomet. Chem. 1999 , 576 , 147{168.
  • 20. Suzuki, A. Chem. Commun. 2005 , 4759{4763.
  • 21. Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002 , 41 , 4176{4211.
  • 22. Phan, N. T. S.; Van Der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006 , 348 , 609{679.
  • 23. Polshettiwar, V.; Decottignies, A.; Len, C.; Fihri, A. Chem. Sus. Chem. 2010 , 3 , 502{522.
  • 24. Slagt, V. F.; De Vries, A. H. M.; De Vries, J. G.; Kellogg, R. M. Org. Process Res. Dev. 2010 , 14 , 30{47.
  • 25. Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2008 , 64 , 3047{3101.
  • 26. Baran, T.; Aciksoz, E.; Mentes, A. J. Mol. Cat. A. 2015 , 407 , 47{52.
  • 27. Das, S.; Bhunia, S.; Maity, T.; Koner, S. J. Mol. Cat. A. 2014 , 394 , 188{197.
  • 28. Tenchiu, A. C.; Ventouri, I. K.; Ntasi, G.; Palles, D.; Kokotos, G.; Demertzi, D. K.; Kostas, I. D. Inorg. Chim. Acta 2015 , 435 , 142{146.
  • 29. Temel, H.; Pasa, S.; Ocak, Y. S.; Yilmaz, I.; Demir, S.; Ozdemir, I. Synthetic Met. 2012 , 161 , 2765{2775.
  • 30. Klncarslan, R.; Karabyk, H.; Ulusoy, M.; Aygun, M.; Cetinkaya, B.; Buyukgungor, O. J. Coord. Chem. 2006 , 59 , 1649{1656.
  • 31. Tas, E.; Aslanoglu, M.; Guler, M.; Ulusoy, M. J. Coord. Chem. 2004 , 57 , 583{589.
  • 32. Littke, A. F.; Fu, G. F. Angew. Chem., Int. Ed. 2002 , 41 , 4176{4211.
  • 33. Bedford, R. B.; Hazelwood, S. L.; Limmert, M. E. Chem. Commun. 2002 , 2610{2611.
  • 34. Stanforth, S. P. Tetrahedron 1998 , 54 , 263{303.
  • 35. Crisp, G. T. Chem. Soc. Rev. 1998 , 27 , 427{436.
  • 36. Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001 , 57 , 7449{7476.
  • 37. Miyaura, N.; Suzuki, A. Chem. Rev. 1995 , 95 , 2457{2483.
  • 38. Suzuki, A. J. Organomet. Chem. 1999 , 576 , 147{168.
  • 39. Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002 , 653 , 69{82.
  • 40. Sahin, C.; Ulusoy, M.; Zafer, C.; Ozsoy, C.; Varlikli, C.; Dittrich, T.; Cetinkaya, B.; Icli, S. Dyes Pigments 2009 , 84 , 88{94.
  • 41. Angay, F.; Celik,  O.; Barlk, O.; Ulusoy, M. Acta Cryst. 2014 , E70 , o563{o564.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

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

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Cross coupling reactions catalyzed by (NHC)Pd(II) complexes

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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

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Contribution of heterobifunctional ligands to transition metal-catalysed C--C coupling reactions

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The synthesis, characterization, and catalytic properties of (2-C,N) palladacycles with N-heterocyclic carbene-based ancillary ligands

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