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TiCl(OiPr)3-mediated One-pot Reductive Amination of 1,1'-Diacetylferrocene with Aryl Amines

  • Ahmad, Md. Wasi (Department of Applied Chemistry, Kyungpook National University) ;
  • Lee, Sang-Yeon (Department of Applied Chemistry, Kyungpook National University) ;
  • Kim, Tae-Jeong (Department of Applied Chemistry, Kyungpook National University) ;
  • Kim, Hong-Seok (Department of Applied Chemistry, Kyungpook National University)
  • Received : 2011.08.26
  • Accepted : 2011.09.15
  • Published : 2011.11.20

Abstract

Keywords

References

  1. Dai, L. X.; Tu, T.; You, S. L.; Deng, W. P.; Hou, X. L. Acc. Chem. Res. 2003, 36, 659. https://doi.org/10.1021/ar020153m
  2. Colacot, T. J. Chem. Rev. 2003, 103, 3101. https://doi.org/10.1021/cr000427o
  3. Sutcliffe, O. B.; Bryce, M. R. Tetrahedron: Asymmetry 2003, 14, 2297. https://doi.org/10.1016/S0957-4166(03)00520-2
  4. Wang, H.-X.; Gao, R.-Q.; Yang, X.-L.; Wan, L.; Wu, H.-F.; Geng, F.-Y.; Jin, R. Polyhedron 2007, 26, 1037. https://doi.org/10.1016/j.poly.2006.09.093
  5. Lee, S. W. J. Organomet. Chem. 2006, 691, 1347. https://doi.org/10.1016/j.jorganchem.2005.12.018
  6. Tremblay, D.; Barrett, F. B.; Taylor, N. J. J. Organomet. Chem. 2006, 691, 2044. https://doi.org/10.1016/j.jorganchem.2006.01.012
  7. Weng, Z.; Teo, S.; Koh, L. L.; Andy Hor, T. S. Organometallics 2004, 23, 3603. https://doi.org/10.1021/om049911y
  8. Gibson, V. C.; Long, N. J.; Marshall, E. L.; Oxford, P. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Dalton Trans. 2001, 1162.
  9. Wu, Y. J.; Cui, X. L.; Zhou, N.; Song, M. P.; Yun, H. Y.; Du, C. X.; Zhu, Y. Tetrahedron: Asymmetry 2000, 11, 4877. https://doi.org/10.1016/S0957-4166(00)00478-X
  10. Bosque, R.; Lopez, C.; Solans, X.; Font-Bardia, M. Organometallics 1999, 18, 1267. https://doi.org/10.1021/om980834e
  11. McGrouther, K.; Weston, D. K.; Fenby, D.; Robinson, B. H.; Simpson, J. J. Chem. Soc., Dalton Trans. 1999, 1957.
  12. Ranatunge-Bandarage, P. R. R.; Robinson, B. H.; Simpson, J. Organometallics 1994, 13, 405.
  13. Khan, S. N.; Kim, B. J.; Kim, H.-S. Bioorg. Med. Chem. Lett. 2007, 17, 5139. https://doi.org/10.1016/j.bmcl.2007.07.001
  14. Grenga, P. N.; Sumbler, B. L.; Beland, F.; Ronny, P. Tetrahedron Lett. 2009, 50, 6658. https://doi.org/10.1016/j.tetlet.2009.09.076
  15. Markey, M. D.; Fu, Y.; Kelly, T. R. Org. Lett. 2007, 9, 3255. https://doi.org/10.1021/ol0711974
  16. Baxter, E. W.; Reitz, A. B. Org. React. 2002, 59, 1.
  17. Lewin, G.; Schaeffer, C. Heterocycles 1998, 48, 171. https://doi.org/10.3987/COM-97-7999
  18. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849. https://doi.org/10.1016/S0040-4039(99)00896-5
  19. Abdel-Magid, A. F.; Mehrman, S. J. Org. Process Res. Dev. 2006, 10, 971. https://doi.org/10.1016/j.tetlet.2007.07.217
  20. Weis, A. L.; Bakos, T.; Alferiev, I.; Zhang, X.; Shao, B.; Kinney, W. A. Tetrahedron Lett. 1999, 40, 4863. https://doi.org/10.1016/S0040-4039(99)00896-5
  21. Cabral, S.; Hulin, B.; Kawai, M. Tetrahedron Lett. 2007, 48, 7134. https://doi.org/10.1016/j.tetlet.2007.07.217
  22. Reddy, P. S.; Kanjilal, S.; Sunitha, S.; Prasad, R. B. N. Tetrahedron Lett. 2007, 48, 8807. https://doi.org/10.1016/j.tetlet.2007.10.094
  23. Alinezhad, H.; Tajbakhsh, M.; Zare, M. Synth. Commun. 2009, 39, 2907. https://doi.org/10.1080/00397910802691882
  24. Khan, S. N.; Bae, S. Y.; Kim, H.-S. Tetrahedron Lett. 2005, 46, 7675. https://doi.org/10.1016/j.tetlet.2005.09.051
  25. Khan, S. N.; Cho, N.-J.; Kim, H.-S. Tetrahedron Lett. 2007, 48, 5189. https://doi.org/10.1016/j.tetlet.2007.05.157
  26. Khan, S. N.; Jung, Y. M.; Kim, B. J.; Cho, H.; Lee, J.; Kim, H.-S. Bioorg. Med. Chem. Lett. 2008, 18, 2558. https://doi.org/10.1016/j.bmcl.2008.03.042
  27. Ahmad, M. W.; Jung, Y. M.; Khan, S. N.; Kim, H.-S. Bull. Korean Chem. Soc. 2009, 30, 2101. https://doi.org/10.5012/bkcs.2009.30.9.2101
  28. Burkhardt, E. R.; Coleridge, B. M. Tetrahedron Lett. 2008, 49, 5152. https://doi.org/10.1016/j.tetlet.2008.06.095
  29. Cho, B. T.; Kang, S. K. Tetrahedron 2005, 61, 5725. https://doi.org/10.1016/j.tet.2005.04.039
  30. Ramachandran, P. V.; Gagare, P. D.; Sakavuyi, K.; Clark, P. Tetrahedron Lett. 2010, 51, 3167. https://doi.org/10.1016/j.tetlet.2010.04.014
  31. Gallou, F.; Han, B.; Lu, J.; Weibel, M. S.; Stoessel, A. F. Tetrahedron Lett. 2010, 51, 1419. https://doi.org/10.1016/j.tetlet.2010.01.029
  32. Salmi, C.; Loncle, C.; Letourneux, Y.; Brunel, J. M. Tetrahedron 2008, 64, 4453. https://doi.org/10.1016/j.tet.2008.02.055
  33. Salmi, C.; Loncle, C.; Vidal, N.; Letourneux, Y.; Brunel, J. M. Eur. J. Med. Chem. 2008, 43, 540. https://doi.org/10.1016/j.ejmech.2007.04.006
  34. Loncle, C.; Salmi, C.; Letournex, Y.; Brunel, J. M. Tetrahedron 2007, 63, 12968. https://doi.org/10.1016/j.tet.2007.10.032
  35. Di-Cesare, J. C.; White, C. E.; Rasmussen, W. E.; White, M. B.; McComas, C. B.; Craft, L. E. Synth. Commun. 2005, 35, 663. https://doi.org/10.1081/SCC-200050354
  36. Miriyala, B.; Bhattacharyya, S.; Williamson, J. S. Tetrahedron 2004, 60, 1463. https://doi.org/10.1016/j.tet.2003.12.024
  37. Bhattacharyya, S.; Neidigh, K. A.; Avery, M. A.; Williamson, J. S. Synlett 1999, 1781. https://doi.org/10.1016/j.tetlet.2005.02.155
  38. Gutierrez, C. D.; Bavetsias, V.; McDonald, E. J. Comb. Chem. 2008, 10, 280. https://doi.org/10.1021/cc700132f
  39. Gutierrez, C. D.; Bavetsias, V.; McDonald, E. Tetrahedron Lett. 2005, 46, 3595. https://doi.org/10.1016/j.tetlet.2005.02.155
  40. Patel, P. J.; Li, A.-H.; Dong, H.; Korlipara, V. L.; Mulvihill, M. J. Tetrahedron Lett. 2009, 50, 5975. https://doi.org/10.1016/j.tetlet.2009.08.048

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