Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Intramolecular Hydroaminations of Aminoalkynes Catalyzed by Yttrium Complexes and Aminoallenes Catalyzed by Zirconium Complexes

  • Kim, Hyun-Seok (Department of Chemistry, Kangwon National University) ;
  • Livinghouse, T. (Department of Chemistry, Montana State University) ;
  • SeoMoon, Dong (Department of Chemistry, Kangwon National University) ;
  • Lee, Phil-Ho (Department of Chemistry, Kangwon National University)
  • Published : 2007.07.20
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Abstract

It was demonstrated that Y[N(TMS)2]3, the neutral yttrium-diamine complex 13 and yttrium-NPS complexes 15 are efficient precatalysts for intramolecular hydroamination of aminoalkynes involving primary amines. Complex 13 and 15 were quantitatively prepared in situ by direct metalation of the ligands 4 and 9 with 1 equiv of Y[N(TMS)2]3 in benzene-d6 at 120 oC for 5 days and 10 days, respectively, via elimination of (TMS)2NH. 5-Exo- and 6-exo-dig intramolecular hydroamination of aminoalkynes using catalyst 12 and 13 proceeded smoothly to give nitrogen-contained cyclic products in good to excellent yields in all cases. In the case of 7- exo-dig intramolecular hydroamination, the desired product was produced in 41% and 48% yields despite the gem-dimethyl effect. However, treatment of catalyst 15 with aminoalkynes (19 and 22) having a methyl substituent at the carbon adjacent to triple bond and 6-exo-dig intramolecular hydroamination of 21 failed to give the desired products. Zirconium-catalyzed intramolecular hydroamination of aminoallenes (25, 27, and 31) with 5 mol% 16 afforded 2-(trans-1-propenyl)pyrrolidine, 2-isopropylenepyrrolidine, and 2-(trans-1- propenyl)piperidine in 96%, 95%, and 93% yield, respectively. However, subjecting 25 to 5 mol% 15 was unsuccessful to produce the desired product.

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References

  1. Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675 https://doi.org/10.1021/cr960433d
  2. Burling, S.; Field, L. D.; Messerle, B. A. Organometallics 2000, 19, 87 https://doi.org/10.1021/om9902737
  3. Muller, T. E.; Grosche, M.; Herdtweck, E.; Pleier, A.-K.; Walter, E.; Yan, Y.-K. Organometallics 2000, 19, 170
  4. Vasen, D.; Salzer, A.; Gerhards, F.; Gais, H.-J.; Sturmer, R.; Bieler, N. H.; Togni, A. Organometallics 2000, 19, 539
  5. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9546 https://doi.org/10.1021/ja002284t
  6. Haak, E.; Siebeneicher, H.; Doye, S. Org. Lett. 2000, 2, 1935 https://doi.org/10.1021/ol006011e
  7. Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923 https://doi.org/10.1021/ja005685h
  8. Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104 https://doi.org/10.1039/b200386b
  9. Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935
  10. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079 https://doi.org/10.1021/cr0201068
  11. Gagne, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108 https://doi.org/10.1021/ja00193a056
  12. Gagne, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716 https://doi.org/10.1021/om00156a005
  13. Gagne, M. R.; Brard, L.; Conticello, V. P.; Giardello, M. A.; Stern, C. L.; Marks, T. J. Organometallics 1992, 11, 2003 https://doi.org/10.1021/om00042a012
  14. Li, Y.; Fu, P.-F.; Marks, T. J. Organometallics 1994, 13, 439
  15. Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagne, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241 https://doi.org/10.1021/ja00101a048
  16. Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707 https://doi.org/10.1021/ja952433l
  17. Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770 https://doi.org/10.1021/om960293y
  18. Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295 https://doi.org/10.1021/ja9612413
  19. Hong, S.; Marks, T. J. J. Am. Chem. Soc. 2002, 124, 7886 https://doi.org/10.1021/ja020226x
  20. Gribkov, D. V.; Hulzsch, K. C.; Hampel, F. Chem. Eur. J. 2003, 9, 4796 https://doi.org/10.1002/chem.200304975
  21. Ryu, J.-S.; Li, G. Y.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 12584 https://doi.org/10.1021/ja035867m
  22. Hong, S.; Tian, S.; Metz, M. V.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 14768 https://doi.org/10.1021/ja0364672
  23. Hong, S.; Kawaoka, A. M.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 15878 https://doi.org/10.1021/ja036266y
  24. Gribkov, D. V.; Hultzsch, K. C. Angew. Chem. Int. Ed. 2004, 43, 5542
  25. Hultzsch, D. K. C.; Hampel, F.; Wagner, T. Organometallics 2004, 23, 2601 https://doi.org/10.1021/om030679q
  26. Gagne, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275 https://doi.org/10.1021/ja00027a036
  27. Molander, G. A.; Dowdy, E. D. J. Org. Chem. 1998, 63, 8983 https://doi.org/10.1021/jo981345r
  28. Tian, S.; Arredondo, V. M.; Stern, C. L.; Marks, T. J. Organometallics 1999, 18, 2568 https://doi.org/10.1021/om990146a
  29. Ruy, J.-S.; Marks, T. J.; McDonald, F. E. Org. Lett. 2001, 3, 3091
  30. Burgstein, M. R.; Berberich, H.; Roesky, P. W. Organometallics 1998, 17, 1452 https://doi.org/10.1021/om9711077
  31. Arredondo, V. M.; Tian, S.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1999, 121, 3633 https://doi.org/10.1021/ja984305d
  32. Duncan, D.; Livinghouse, T. Organometallics 1999, 18, 4421 https://doi.org/10.1021/om9902380
  33. Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 39, 673
  34. Ryu, J.-S.; Marks, T. J.; McDonald, F. E. J. Org. Chem. 2004, 69, 1038 https://doi.org/10.1021/jo035417c
  35. Kim, Y. K.; Livinghouse, T.; Bercaw, J. E. Tetrahedron Lett. 2001, 42, 2933 https://doi.org/10.1016/S0040-4039(01)00346-X
  36. Kim, Y. K.; Livinghouse, T. Angew. Chem. Int. Ed. 2002, 41, 3645 https://doi.org/10.1002/1521-3773(20021004)41:19<3645::AID-ANIE3645>3.0.CO;2-F
  37. Kim, Y. K.; Livinghouse, T.; Horino, Y. J. Am. Chem. Soc. 2003, 125, 9560 https://doi.org/10.1021/ja021445l
  38. Kim, H.; Lee, P. H.; Livinghouse, T. Chem. Commun. 2005, 5205
  39. Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 4391 https://doi.org/10.1021/ol051574h
  40. Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 1737 https://doi.org/10.1021/ol050294z
  41. Kim, H.; Livinghouse, T.; Shim, J. H.; Lee, S. G.; Lee, P. H. Adv. Synth. Catal. 2006, 348, 701 https://doi.org/10.1002/adsc.200505448
  42. Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967 https://doi.org/10.1021/om010566b
  43. Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475 https://doi.org/10.1021/ol0256724
  44. Ackermann, L.; Bergman, R. G.; Loy, R. N. J. Am. Chem. Soc. 2003, 125, 11956 https://doi.org/10.1021/ja0361547
  45. Hoover, J. M.; Petersen, J. R.; Pikul, J.; Johnson, A. R. Organometallics 2004, 23, 4614 https://doi.org/10.1021/om049564s
  46. Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Wiley: New York, 1980
  47. Burgstein, M. R.; Berberich, H.; Roesky, P. W. Chem. Eur. J. 2001, 7, 3078 https://doi.org/10.1002/1521-3765(20010716)7:14<3078::AID-CHEM3078>3.0.CO;2-E
  48. Ward, B. D.; Maisse-Francois, A.; Mountford, P.; Gade, L. H. Chem. Commun. 2004, 704
  49. Li, Y.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2004, 126, 1794 https://doi.org/10.1021/ja038320g

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