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

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

Two mono-benzimidazolium salts of resorcinarene have been prepared and used as ligands in Suzuki{Miyaura cross-coupling reactions. They have been fully characterized by 1 H and 13 C NMR, MALDI, and FT-IR spectroscopic methods, and their structures were con rmed by X-ray diffraction analysis. These two new resorcinarene-based mono- benzimidazolium salts showed good catalytic activity for coupling reactions in DMF. The highest conversion was achieved for arylation of 4-bromotoluene using the resorcinarenyl mono-dimethylbenzimidazolium salt.

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  • 1. Grushin, V. V.; Alper, H. In: Topics in Organometallic Chemistry, Vol. 3 ; Murai, S., Ed. Springer: New York, NY, USA, 1999, pp. 193{226.
  • 2. Beller, M.; Riermeier, T. H. In: Transition Metals for Organic Synthesis, Vol. 1 ; Beller, M.; Bolm, C., Eds. Wiley- VCH: Weinheim, Germany, 1998, pp. 184{193.
  • 3. Suzuki, A. J. Organomet. Chem . 1999 , 576 , 147{168.
  • 4. Kim, Y. H.; Webster, W. W. J. Am. Chem. Soc . 1990 , 112 , 4592{4593.
  • 5. Martin, R.; Buchwald, S. L. Acc. Chem. Res. , 2008 , 41, 1461{1473.
  • 6.  Ozdemir, _ I.; Cetinkaya, B.; Demir, S.; Gurbuz, N. Catal. Lett . 2004 , 97 , 37{40.
  • 7.  Ozdemir, _ I.; Cetinkaya, B.; Demir, S. J. Mol. Cat. A 2004 , 208 , 109{114.
  • 8. Turkmen, H.; Can, R.; Cetinkaya, B. Dalton Trans . 2009 , 7039{7044.
  • 9. Huang, W.; Guo, E. P.; Xiao, Y. J.; Zhu, M. F.; Zou, G.; Tang, J. Tetrahedron 2005 , 61 , 9783{9790.
  • 10.  Ozdemir, _ I.; Gok, Y.; Gurbuz, N.; Cetinkaya, E.; Cetinkaya, B. Synth. Commun. 2004 , 34 , 4135{4144.
  • 11. Zakharova, L. Y.; Valeeva, F. G.; Ibragimova, A. R.; Voronin, M. A.; Kudryavtseva, L. A.; Syakaev, V. V.; Kazakova, E. K.; Morozova, Y. E.; Makarova, N. A.; Mel'nikova, N. B. et al. Russ. Chem. Bull. Int. Ed. 2008 , 57 , 374{382.
  • 12. Zakharova, L. Y.; Syakaev, V. V.; Voronin, M. A.; Valeeva, F. G.; Ibragimova, A. R.; Ablakova, Y. R.; Kazakova, E. K.; Latypov, S. K.; Konovalov, A. I. J. Phys. Chem. C 2009 , 113 , 6182{6190.
  • 13. Pashirova, T. N.; Lukashenko, S. S.; Kosacheva, E. M.; Rizvanova, L. Z.; Gainanova, G. A.; Knyazeva, I. R.; Burilov, A. R.; Kudryavtseva, L. A.; Konovalov, A. I. Russ. Chem. Bull. Int. Ed. 2007 , 56 , 959{966.
  • 14. Pashirova, T. N.; Lukashenko, S. S.; Kosacheva, E. M.; Leonova, M. V.; Vaganova, L. I.; Burilov, A. R.; Pudovik, M. A.; Kudryavtseva, L. A.; Konovalov, A. I. Russ. J. Gen. Chem . 2008 , 78 , 402{409.
  • 15. Shirakawa, S.; Shimizu, S. Synlett 2008 , 10 , 1539{1542.
  • 16. Arnott, G.; Hunter, R.; Su, H. Tetrahedron 2006 , 62 , 977{991.
  • 17. Arnott, G.; Hunter, R. Tetrahedron 2006 , 62 , 992{1000.
  • 18. Sahin, N.; Semeril, D.; Brenner, E.; Matt, D.;  Ozdemir, I.; Kaya, C.; Toupet, L. Chem. Cat. Chem . 2013 , 5 , 1116{1125.
  • 19. El Moll, H.; Semeril, D.; Matt, D.; Youinou, M. T.; Toupet, L. Org. Biomol. Chem . 2009 , 7 , 495{501.
  • 20. El Moll, H.; Semeril, D.; Matt, D.; Toupet, L. Eur. J. Org. Chem . 2010 , 1158{1168.
  • 21. El Moll, H.; Semeril, D.; Matt, D.; Toupet, L. Adv. Synth. Catal . 2010 , 352 , 901{908.
  • 22. El Moll, H.; Semeril, D.; Matt, D.; Toupet, L.; Harrow eld, J. J. Org. Biomol. Chem . 2012 , 10 , 372{382.
  • 23. Frank, M.; Maas, G.; Schatz, J. Eur. J. Org. Chem . 2004 , 607{613.
  • 24. Frank, M.; Maas, G.; Schatz, J. Eur. J. Org. Chem . 2006 , 2378{2383.
  • 25. Dinares, I.; Garcia de Miguel, C.; Font-Bardia, M.; Solans, X.; Alcalde, E. Organometallics 2007 , 26 , 5125{5128.
  • 26. Brenner, E.; Matt, D.; Henrion, M.; Teci, M.; Toupet, L. Dalton Trans . 2011 , 40 , 9889{9898.
  • 27. Fahlbusch, T.; Frank, M.; Schatz, J.; Schuhle, D. T. J. Org. Chem . 2006 , 71 , 1688{1691.
  • 28. Ren, H.; Xu, Y.; Jeanneau, E.; Bonnamour, I.; Tu, T.; Darbost, U. Tetrahedron 2014 , 70 , 2829{2837.
  • 29. Reetz, M. T.; Kostas, I. D.; Waldvogel, S. R. Inorg. Chem. Commun . 2002 , 5 , 252{254.
  • 30. Engeldinger, E.; Poorters, L.; Armspach, D.; Matt, D.; Toupet, L. Chem. Commun . 2004 , 634{635.
  • 31. Legrand, F. X.; Six, N.; Slomianny, C.; Bricout, H.; Tilloy, S.; Mon ier, E. Adv. Synth. Catal. 2011 , 353 , 1325{1334.
  • 32. Tran, D. N.; Legrand, F. X.; Menuel, S.; Bricout, H.; Tilloy, S.; Mon ier, E. Chem. Commun . 2012 , 48 , 753{755.
  • 33. Armspach, D.; Matt, D. Chem. Commun . 1999 , 1073{1074.
  • 34. Engeldinger, E.; Armspach, D.; Matt, D. Angew. Chem. Int. Ed . 2001 , 40 , 2526{2529.
  • 35. Wong, Y. T.; Yang, C.; Ying, K. C.; Ji, G. Organometallics 2002 , 21 , 1782{1787.
  • 36. Engeldinger, E.; Armspach, D.; Matt, D.; Jones, P. G.; Welter, R. Angew. Chem. Int. Ed. 2002 , 41 , 2593{2596.
  • 37. Poorters, L.; Armspach, D.; Matt, D.; Toupet, L.; Choua, S.; Turek, P. Chem. Eur. J. 2007 , 13 , 9448{9461.
  • 38. Guieu, S.; Zaborova, E.; Bleriot, Y.; Poli, G.; Jutand, A.; Madec, D.; Prestat, G.; Sollogoub, M. Angew. Chem. Int. Ed . 2010 , 49 , 2314{2318.
  • 39. Poorters, L.; Armspach, D.; Matt, D.; Toupet, L. Dalton Trans . 2007 , 3195{3202.
  • 40. Gibson, C.; Rebek, J. Org. Lett . 2002 , 4 , 1887{1890.
  • 41. Taskran, D. T.; Dumoulin, F.; Ahsen, V.; _ Isci,  U. Dalton Trans . 2014 , 43 , 2032{2037.
  • 42. Huang, W.; Guo, J.; Xiao, Y.; Zhu, M.; Zou, G.; Tang, J. Tetrahedron 2005 , 61 , 9783{9790.
  • 43. Patil, S.; Deally, A.; Gleeson, B.; Muller-Bunz, H.; Paradisi, F.; Tacke, M. Metallomics 2011 , 3 , 74{88.
  • 44. Bruker. APEX2, Version 2013.10-0. Bruker AXS Inc.: Madison, WI, USA, 2014.
  • 45. Bruker. SAINT, Version 8.34A. Bruker AXS Inc.: Madison, WI, USA, 2013.
  • 46. Bruker. SADABS, Version v2014/2. Bruker AXS Inc.: Madison, WI, USA, 2014.
  • 47. Agilent Technologies. CrysAlisPRO, Version 1.171.37.31 (Release 14-01-2014 CrysAlis171 .NET). Agilent Tech- nologies: Santa Clara, CA, USA, 2011).
  • 48. Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Spagna, R. J. Appl. Cryst . 2005 , 38 , 381{388.
  • 49. Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.; Prout, K.; Watkin, D. J. J. Appl. Cryst. 2003 , 36 , 1487.
  • 50. Spek, A. L. Acta Cryst. D 2009 , 65 , 148{155.
  • 51. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Cryst . 2006 , 39 , 453{457.
  • 52. Perrin, D. D.; Armarego, W. L. F. Puri cation of Laboratory Chemicals , 2nd ed.; Pergamon Press: Oxford, UK, 1989.
  • 53.  Ozdemir, _ I.; Sahin, N.; Gok, Y.; Demir, S.; Cetinkaya, B. J. Mol. Catal. A-Chem . 2005 , 234 , 181{185.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
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