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Polystyrene-supported cu(II)-R-Box as recyclable catalyst in asymmetric Friedel–Crafts reaction

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Abstract

The complex of copper(II) trifluoromethanesulfonate with chiral isopropyl bis(oxazoline) ligand (i-Pr-Box) was immobilized on accessible and inexpensive Merrifield resin according to a “click” procedure. The resulting catalyst showed high efficiency and recyclability in the asymmetric Friedel–Crafts alkylation of indole and its derivatives. The catalyst can be recycled five times without appreciable loss in activity and enantioselectivity.

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References

  1. Asymmetric Catalysis In Organic Synthesis, Noyori, R., Ed., New York: Wiley, 1994.

  2. Bates, R., Organic Synthesis Using Transition Metals, New York: Wiley, 2012.

    Book  Google Scholar 

  3. Lewis Acids in Organic Synthesis, Yamamoto, H., Ed., New York: Wiley, 2008.

  4. Kampen, D., Reisinger, C., and List, B., Asymmetric Organocatalysis (Topics in Current Chemistry, vol. 291), List, B., Ed., Berlin: Springer, 2009, p. 1.

  5. Comprehensive Enantioselective Organocatalysis: Catalysi., Reactions, and Applications, Dalko, P.I., Ed., New York: Wiley, 2013, p. 3.

  6. Szekely, G., de Sousa, M.C.A., Gil, M., Ferreira, F.C., and Heggie, W., Chem. Rev., 2015, vol. 115, p. 8182.

    Article  CAS  Google Scholar 

  7. Fan, Q.-H., Li, Y.-M., and Chan, A.S.C., Chem. Rev., 2002, vol. 102, p. 3385.

    Article  CAS  Google Scholar 

  8. Trindade, A.F., Gois, P.M.P., and Afonso, C.A.M., Chem. Rev., 2009, vol. 109, p. 418.

    Article  CAS  Google Scholar 

  9. Itsuno, S. and Hassan, M.M., RSC Adv., 2014, vol. 4, p. 52023.

    Article  CAS  Google Scholar 

  10. Desimoni, G., Faita, G., and Jørgensen, K.A., Chem. Rev., 2006, vol. 106, p. 3561.

    Article  CAS  Google Scholar 

  11. Johnson, J.S. and Evans, D.A., Acc. Chem. Res., 2000, vol. 33, p. 325.

    Article  CAS  Google Scholar 

  12. Desimoni, G., Faita, G., and Quadrelli, P., Chem. Rev., 2003, vol. 103, p. 3119.

    Article  CAS  Google Scholar 

  13. Rasappan, R., Laventine, D., and Reiser, O., Coord. Chem. Rev., 2008, vol. 252, p. 702.

    Article  CAS  Google Scholar 

  14. Rechavi, D. and Lemaire, M., Chem. Rev., 2002, vol. 102, p. 3467.

    Article  CAS  Google Scholar 

  15. Fraile, J.M., García, J.I., and Mayoral, J.A., Coord. Chem. Rev., 2008, vol. 252, p. 624.

    Article  CAS  Google Scholar 

  16. Burguete, M.I., Fraile, J.M., García, J.I., García-Verdugo, E., Herrerías, C.I., Luis, S.V., and Mayoral, J.A., J. Org. Chem., 2001, vol. 66, p. 8893.

    Article  CAS  Google Scholar 

  17. Silva, A.R., Guimarães, V., Carneiro, L., Nunes, N., Borges, S., Pires, J., Martins, Â., and Carvalho, A.P., Microporous Mesoporous Mater., 2013, vol. 179, p. 231.

    Article  CAS  Google Scholar 

  18. Clarke, R.J. and Shannon, I.J., Chem. Commun., 2001, p. 1936.

    Google Scholar 

  19. Diéz-Barra, E., Fraile, J.M., Garciá, J.I., Garciá-Verdugo, E., Herreriás, C.I., Luis, S.V., Mayoral, J.A., Sánchez-Verdú, P., and Tolosa, J., Tetrahedron: Asymmetry, 2003, vol. 14, p. 773.

    Article  Google Scholar 

  20. Langham, C., Piaggio, P., McMorn, P., Willock, D.J., Hutchings, G.J., Bethell, D., Lee, D.F., Bulman Page, P.C., Sly, C., Hancock, F.E., and King, F., Chem. Commun., 1998, p. 1601.

    Google Scholar 

  21. Sakthivel, A., Hijazi, A.K., Hanzlik, M., Chiang, A.S.T., and Kühn, F.E., Appl. Catal., A, 2005, vol. 294, p. 161.

    Article  CAS  Google Scholar 

  22. Annunziata, R., Benaglia, M., Cinquini, M., Cozzi, F., and Pitillo, M., J. Org. Chem., 2001, vol. 66, p. 3160.

    Article  CAS  Google Scholar 

  23. Fraile, J.M., García, N., and Herrerías, C.I., ACS Catalysis, 2013, vol. 3, p. 2710.

    Article  CAS  Google Scholar 

  24. Orlandi, S., Benaglia, M., Dell’Anna, G., and Celentano, G., J. Organomet. Chem., 2007, vol. 692, p. 2120.

    Article  CAS  Google Scholar 

  25. Fraile, J.M., Pérez, I., Mayoral, J.A., and Reiser, O., Adv. Synth. Catal., 2006, vol. 348, p. 1680.

    Article  CAS  Google Scholar 

  26. Fraile, J.M., Pérez, I., and Mayoral, J.A., J. Catal., 2007, vol. 252, p. 303.

    Article  CAS  Google Scholar 

  27. Lee, J.-M., Kim, J., Shin, Y., Yeom, C.-E., Lee, J.E., Hyeon, T., and Moon Kim, B., Tetrahedron: Asymmetry, 2010, vol. 21, p. 285.

    Article  CAS  Google Scholar 

  28. Torres-Werle, M., Nano, A., Maisse-Francois, A., and Bellemin-Laponnaz, S., New J. Chem., 2014, vol. 38, p. 4748.

    Article  CAS  Google Scholar 

  29. Lee, A., Kim, W., Lee, J., Hyeon, T., and Kim, B.M., Tetrahedron: Asymmetry, 2004, vol. 15, p. 2595.

    Article  CAS  Google Scholar 

  30. Rasappan, R., Olbrich, T., and Reiser, O., Adv. Synth. Catal., 2009, vol. 351, p. 1961.

    Article  CAS  Google Scholar 

  31. Liu, H. and Du, D.M., Eur. J. Org. Chem., 2010, p. 2121.

    Google Scholar 

  32. Corma, A., Garcia, H., Moussaif, A., Sabater, M.J., Zniber, R., and Redouane, A., Chem. Commun., 2002, p. 1058.

    Google Scholar 

  33. Glos, M. and Reiser, O., Org. Lett., 2000, vol. 2, p. 2045.

    Article  CAS  Google Scholar 

  34. Hager, M., Wittmann, S., Schätz, A., Pein, F., Kreitmeier, P., and Reiser, O., Tetrahedron: Asymmetry, 2010, vol. 21, p. 1194.

    Article  CAS  Google Scholar 

  35. Zhuang, W., Hansen, T., and Jørgensen, K.A., Chem. Commun., 2001, p. 347.

    Google Scholar 

  36. Jørgensen, K.A., Synthesis, 2003, p. 1117.

    Google Scholar 

  37. Poulsen, T.B. and Jørgensen, K.A., Chem. Rev., 2008, vol. 108, p. 2903.

    Article  CAS  Google Scholar 

  38. Meldal, M. and Tornøe, C.W., Chem. Rev., 2008, vol. 108, p. 2952.

    Article  CAS  Google Scholar 

  39. Schätz, A., Grass, R.N., Kainz, Q., Stark, W.J., and Reiser, O., Chem. Mater., 2010, vol. 22, p. 305.

    Article  Google Scholar 

  40. Schätz, A., Hager, M., and Reiser, O., Adv. Funct. Mater., 2009, vol. 19, p. 2109.

    Article  Google Scholar 

  41. Gaab, M., Bellemin-Laponnaz, S., and Gade, L.H., Chem. Eur. J., 2009, vol. 15, p. 5450.

    Article  CAS  Google Scholar 

  42. Chan, T.R., Hilgraf, R., Sharpless, K.B., and Fokin, V.V., Org. Lett., 2004, vol. 6, p. 2853.

    Article  CAS  Google Scholar 

  43. Zhou, J. and Tang, Y., Chem. Commun., 2004, p. 432.

    Google Scholar 

  44. Zhou, J., Ye, M.-C., Huang, Z.-Z., and Tang, Y., J. Org. Chem., 2004, vol. 69, p. 1309.

    Article  CAS  Google Scholar 

  45. Yamazaki, S. and Iwata, Y., J. Org. Chem., 2006, vol. 71, p. 739.

    Article  CAS  Google Scholar 

  46. Wu, J., Wang, D., Wu, F., and Wan, B., J. Org. Chem., 2013, vol. 78, p. 5611.

    Article  CAS  Google Scholar 

  47. Wen, L., Shen, Q., Wan, X., and Lu, L., J. Org. Chem., 2011, vol. 76, p. 2282.

    Article  CAS  Google Scholar 

  48. Zhou, Y.-Y., Sun, X.-L., Zhu, B.-H., Zheng, J.-C., Zhou, J.-L., and Tang, Y., Synlett, 2011, p. 935.

    Google Scholar 

  49. Sun, Y.-J., Li, N., Zheng, Z.-B., Liu, L., Yu, Y.-B., Qin, Z.-H., and Fu, B., Adv. Synth. Catal., 2009, vol. 351, p. 3113.

    Article  CAS  Google Scholar 

  50. Liu, L., Li, J., Wang, M., Du, F., Qin, Z., and Fu, B., Tetrahedron: Asymmetry, 2011, vol. 22, p. 550.

    Article  CAS  Google Scholar 

  51. Liu, L., Ma, H.L., Xiao, Y.M., Du, F.P., Qin, Z.H., Li, N., and Fu, B., Chem. Commun., 2012, vol. 48, p. 9281.

    Article  CAS  Google Scholar 

  52. Desimoni, G., Faita, G., and Quadrelli, P., Chem. Rev., 2013, vol. 113, p. 5924.

    Article  CAS  Google Scholar 

  53. Shiri, M., Heravi, M.M., and Soleymanifard, B., Tetrahedron, 2012, vol. 68, p. 6593.

    Article  CAS  Google Scholar 

  54. Liu, Y.L., Shang, D.J., Zhou, X., Zhu, Y., Lin, L.L., Liu, X.H., and Feng, X.M., Org. Lett., 2010, vol. 12, p. 180.

    Article  Google Scholar 

  55. Jensen, K.B., Thorhauge, J., Hazell, R.G., and Jørgensen, K.A., Angew. Chem., Int. Ed., 2001, vol. 40, p. 160.

    Article  CAS  Google Scholar 

  56. Ma, H.L., Li, J.Q., Sun, L., Hou, X.H., Zhang, Z.H., and Fu, B., Tetrahedron, 2015, vol. 71, p. 3625.

    Article  CAS  Google Scholar 

  57. Epifano, F., Genovese, S., Rosati, O., Tagliapietra, S., Pelucchini, C., and Curini, M., Tetrahedron Lett., 2011, vol. 52, p. 568.

    Article  CAS  Google Scholar 

  58. Li, J., Chen, H.L., Liu, L., and Fu, B., Molecules, 2010, vol. 15, p. 8582.

    Article  CAS  Google Scholar 

  59. Liu, Y.L., Shang, D.J., Zhou, X., Liu, X.H., and Feng, X.M., Chem. Eur. J., 2009, vol. 15, p. 2055.

    Article  CAS  Google Scholar 

  60. Harrington, P. and Kerr, M.A., Can. J. Chem., 1998, vol. 76, p. 1256.

    Article  CAS  Google Scholar 

  61. Schatz, A., Rasappan, R., Hager, M., Gissibl, A., and Reiser, O., Chem. Eur. J., 2008, vol. 14, p. 7259.

    Article  Google Scholar 

  62. Jia, S.J. and Du, D.M., Tetrahedron: Asymmetry, 2014, vol. 25, p. 980.

    Article  CAS  Google Scholar 

  63. Desimoni, G., Faita, G., Toscanini, M., and Boiocchi, M., Chem. Eur. J., 2008, vol. 14, p. 3630.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Leninskie gory 1, Moscow, 119991, Russia

    V. G. Desyatkin, M. V. Anokhin & I. P. Beletskaya

  2. King Abdullah University of Science and Technology, Thuwal, 23955-6900, Saudi Arabia

    V. O. Rodionov

Authors
  1. V. G. Desyatkin
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  2. M. V. Anokhin
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  3. V. O. Rodionov
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  4. I. P. Beletskaya
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Correspondence to I. P. Beletskaya.

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Original Russian Text © V.G. Desyatkin, M.V. Anokhin, V.O. Rodionov, I.P. Beletskaya, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 12, pp. 1727–1737.

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Desyatkin, V.G., Anokhin, M.V., Rodionov, V.O. et al. Polystyrene-supported cu(II)-R-Box as recyclable catalyst in asymmetric Friedel–Crafts reaction. Russ J Org Chem 52, 1717–1727 (2016). https://doi.org/10.1134/S1070428016120010

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  • DOI: https://doi.org/10.1134/S1070428016120010

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