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Bifunctional Salen-Cu(II) complex as efficient catalyst for N-arylation of imidazoles and Suzuki-Miyaura coupling reactions

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Abstract

Bifunctional Salen-Cu(II) complex catalyzed cross-coupling reactions of aryl halids with imidazoles or phenylboronic acid reagents have been developed as practical methods for C―N and C―C bond formation. The procedure tolerates aryl halides with various functional groups(such as methoxy, acetyl, nitrile, fluoro and nitro groups) and gives the corresponding coupling products in moderate to high yields. The catalyst remained active after five successive catalytic runs without loss in performance.

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References

  1. Thomas K. R. J., Lin J. T., Tao Y. T., Ko C. W., J. Am. Chem. Soc., 2001, 123(123), 9404

    Article  CAS  Google Scholar 

  2. Ley S. V., Thomas A. W., Angew. Chem. Int. Ed., 2003, 42(42), 5400

    Article  CAS  Google Scholar 

  3. Kinzel T., Zhang Y., Buchwald S. L., J. Am. Chem. Soc., 2010, 132(132), 14073

    Google Scholar 

  4. Ghosh R., Adarsh N. N., Sarkar A., J. Org. Chem., 2010, 75(75), 5320

    Article  CAS  Google Scholar 

  5. Fliedel C., Braunstein P., Organometallics, 2010, 29(29), 5614

    Article  CAS  Google Scholar 

  6. Huynh H. V., Yeo C. H., Chew Y. X., Organometallics, 2010, 29(29), 1479

    Article  CAS  Google Scholar 

  7. Karimi B., Akhavan P. F., Chem. Commun., 2009, (25), 3750

  8. Alonso D. A., Nájera C., Pacheco M. C., J. Org. Chem., 2002, 67(67), 5588

    Article  CAS  Google Scholar 

  9. Alonso D. A., Nájera C., Pacheco M. C., Org. Lett., 2000, 2(2), 1823

    Article  CAS  Google Scholar 

  10. Zhou J., Li X., Sun H., J. Organometal. Chem., 2010, 695(695), 297

    Article  CAS  Google Scholar 

  11. Chen C. L., Liu Y. H., Peng S. M., Liu S. T., Organometallics, 2005, 24(24), 1075

    Article  CAS  Google Scholar 

  12. Cui J., Zhang M., Zhang Y., Inorg. Chem. Commun., 2010, 13, 81

    Article  CAS  Google Scholar 

  13. Schnyder A., Indolese A. F., Studer M., Blaser H. U., Angew. Chem. Int. Ed., 2002, 41(41), 3668

    Article  CAS  Google Scholar 

  14. Dai M., Liang B., Wang C., Chen J., Yang Z., Org. Lett., 2004, 6(6), 221

    Article  CAS  Google Scholar 

  15. Ma D., Cai Q., Acc. Chem. Res., 2008, 41(41), 1450

    Article  CAS  Google Scholar 

  16. Siddle J. S., Batsanov A. S., Bryce M. R., Eur., J. Org. Chem., 2008, 16, 2746

    Article  Google Scholar 

  17. Wu M., Mao J., Gou J., Ji S., Eur. J. Org. Chem., 2008, 23, 4050

    Article  Google Scholar 

  18. Suresh P., Pitchuman K., J. Org. Chem., 2008, 73(73), 9121

    Article  CAS  Google Scholar 

  19. Jammi S., Sakthivel S., Rout L., Mukherjee T., Mandai S., Mitra R., Saha P., Punniyamurthy T., J. Org. Chem., 2009, 74, 1971

    Article  CAS  Google Scholar 

  20. Strieter E. R., Bhayana B., Buchwald S. L., J. Am. Chem. Soc., 2009, 131(131), 12898

    Google Scholar 

  21. Cristau H. J., Cellier P. P., Spindler J. F., Taillefer M., Eur. J. Org. Chem., 2004, 695

  22. Cristau H. J., Cellier, P. P. Sp indler J. F., Taillefer M., Chem. Eur. J., 2004, 10(10), 5607

    Article  CAS  Google Scholar 

  23. Monnier F., Taillefer M., Angew. Chem. Int. Ed., 2008, 47(47), 3096

    Article  CAS  Google Scholar 

  24. Khare S., Chokhare R., J. Mol. Cat. A: Chem., 2012, 353, 138

    Article  Google Scholar 

  25. Chai L. Q., Wang G., Sun Y. X., Dong W. K., Zhao L., Gao X. H., J. Coord. Chem., 2012, 65, 1621

    Article  CAS  Google Scholar 

  26. Zeynep T., Mahmut U., J. Organometal. Chem., 2012, 713, 104

    Article  Google Scholar 

  27. Olav S., Guido C. H., Thomas C., Stephan R., Angew. Chem. Int. Ed., 2010, 49(49), 4927

    Google Scholar 

  28. Minutolot F., Pinit D., Petri A., Salvadort P., Tetrahedron: Asymmetry, 1996, 7(7), 2293

    Article  Google Scholar 

  29. Bahramian B., Mirkhani V., Moghadam M., Tangestaninejad S., Cat. Commun., 2006, 7, 289

    Article  CAS  Google Scholar 

  30. Campeau L. C., Fagnou K., Chem. Soc. Rev., 2007, 36(36), 1058

    Article  CAS  Google Scholar 

  31. Wiglenda T., Gust R., J. Med. Chem., 2007, 50(50), 1475

    Article  CAS  Google Scholar 

  32. Kison C., Opatz T., Chem. Eur. J., 2009, 15(15), 843

    Article  CAS  Google Scholar 

  33. Wang Z., Skerlj R. T., Bridger G. J., Tetrahedron Lett., 1999, 40(40), 3543

    Article  CAS  Google Scholar 

  34. Mann G., Hartwig J. F., Tetrahedron Lett., 1997, 38(38), 8005

    Article  CAS  Google Scholar 

  35. Wolter M., Nordmann G., Job G. E., Buchwald S. L., Org. Lett., 2002, 4(4), 973

    Article  CAS  Google Scholar 

  36. Nordmann G., Buchwald S. L., J. Am. Chem. Soc., 2003, 125(125), 4978

    Article  CAS  Google Scholar 

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Correspondence to Yi Wang.

Additional information

Supported by the National Natural Science Foundation of China(No.20672054) and the Scientific Research Fund of Yunnan Provincial Department of Education, China(No.22012Z020).

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Wang, Y., Gao, J., Zhao, M. et al. Bifunctional Salen-Cu(II) complex as efficient catalyst for N-arylation of imidazoles and Suzuki-Miyaura coupling reactions. Chem. Res. Chin. Univ. 31, 549–552 (2015). https://doi.org/10.1007/s40242-015-4437-3

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  • DOI: https://doi.org/10.1007/s40242-015-4437-3

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