Direct palladium(0)-catalyzed amination of allylic alcohols with aminonaphthalenes

Tetrahedron Letters

Volumn 44, Issue 7, 2003, Pages 1481-1485

  Shue, Yi Jen ^a   Yang, Shyh Chyun ^a   Lai, Hwe Chen ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL COMPOUND; AMINE; CARBON; NAPHTHALENE DERIVATIVE; NAPHTHYL GROUP; OXYGEN; PALLADIUM COMPLEX; TITANIUM DERIVATIVE;

ALLYLATION; AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND;

EID: 0037429102     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02861-7     Document Type: Article

References (74)

1. Collman J.P., Hegedus L.S., Norton J.R., Finke R.G. Principles and Applications of Organotransition Metal Chemistry. 1987;University Science Books, Mill Valley, CA.
2. One reaction of this type is the hydroamination of alkenes and alkynes. For leading references see the following nine citations: (a) Hegedus, L. S.; Allen, G. F.; Bozell, J. J.; Waterman, E. L. J. Am. Chem. Soc. 1978, 100, 5800;
3. (b) Pez, G. P.; Galle, J. E. Pure Appl. Chem. 1985, 57, 1917;
4. (c) catalysis with a low-valent arylamido complex has been reported, although turnover numbers are not high: Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738 and references cited therein;
5. (d) Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108;
6. (e) Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716;
7. (f) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708;
8. (g) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459;
9. (h) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753;
10. (i) Brunet, J.; Commenges, G.; Neibecker, D.; Philippot, K. J. Organomet. Chem. 1994, 469, 221.
11. Gilson M.S., Bradshaw W. Angew. Chem., Int. Ed. Engl. 7:1968;919.
12. For instance: (a) Chiusoli, G. P.; Salerno, G. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R.; Patai, S., Eds.; John Wiley & Sons: Chichester, UK, 1985; Vol. 3, Chapter 3.1, p. 143;
13. (b) Tsuji, J. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R.; Patai, S., Eds.; John Wiley & Sons: Chichester, UK, 1985; Vol. 3, Chapter 3.2, p. 163;
14. (c) Sato, F. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R.; Patai, S., Eds.; John Wiley & Sons: Chichester, UK, 1985; Vol. 3, Chapter 3.3, p. 200;
15. (d) Bäckvall, J. E. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1, p. 135.
16. (a) Heck R.F. Palladium Reagents in Organic Synthesis; Academic Press, London, 1985;
17. (b) Goldeski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3;
18. (c) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-Assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2;
19. (d) Tsuji J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995.
20. (a) Connell R.D., Rein T., Åkermark B., Helquist P. J. Org. Chem. 1988 53, 3845;
21. (b) Sakamoto M., Shimizu I., Yamamoto A. Bull. Chem. Soc. Jpn. 1996, 69, 1065.
22. Trost B.M. Acc. Chem. Res. 13:1980;385.
23. Backvall J.E. Acc. Chem. Res. 16:1983;335.
24. Tsuji M., Minami I. Acc. Chem. Res. 20:1987;140.
25. Tsuji M., Minami I. Acc. Chem. Res. 20:1987;140.
26. Trost B.M. Angew. Chem., Int. Ed. Engl. 28:1989;1173.
27. Oppolzer W. Angew. Chem., Int. Ed. Engl. 28:1989;38.
28. Tsuji J. Synthesis. 1990;739.
29. Trost B.M. Pure Appl. Chem. 64:1992;315.
30. Backvall J.E. Pure Appl. Chem. 64:1992;429.
31. Frost C.G., Howarth J., Williams J.M.J. Tetrahedron: Asymmetry. 3:1992;1089.
32. Giambastiani G., Poli G. J. Org. Chem. 63:1998;9608.
33. Uozumi Y., Danjo H., Hayashi T. J. Org. Chem. 64:1999;3384.
34. Tsuji J., Shimizu I., Minami I., Ohashi Y. Tetrahedron Lett. 23:1982;4809.
35. Trost B.M., Hung M.H. J. Am. Chem. Soc. 105:1983;7757.
36. Takahashi T., Jinbo Y., Kitamura K., Tsuji J. Tetrahedron Lett. 25:1984;5921.
37. Tsuji J., Shimizu I., Minami I., Ohashi Y., Sugiura T., Takahashi K. J. Org. Chem. 50:1985;1523.
38. Stary I., Kocovsky P. J. Am. Chem. Soc. 111:1989;4981.
39. Stary I., Zajicek J., Kocovsky P. Tetrahedron. 48:1992;7229.
40. Goux C., Massacret M., Lhoste P., Sinou D. Organometallics. 14:1995;4585.
41. Deardorff D.R., Savin K.A., Justman C.J., Karanjawala Z.E., Sheppeck J.E. II, Hager D.C., Aydin N. J. Org. Chem. 61:1996;3616.
42. Moreno-Manas M., Morral L., Pleixats R. J. Org. Chem. 63:1998;6160.
43. Minami I., Ohashi Y., Shimizu I., Tsuji J. Tetrahedron Lett. 26:1985;2449.
44. Minami I., Yuhara M., Tsuji J. Tetrahedron Lett. 28:1987;2737.
45. Hayashi T., Yamamoto A., Ito Y. Tetrahedron Lett. 28:1987;4837.
46. Ziegler F.E., Kneisley A., Wester R.T. Tetrahedron Lett. 27:1986;1221.
47. Ziegler F.E., Wester R.T. Tetrahedron Lett. 27:1986;1225.
48. Ziegler F.E., Cain W.T., Kneisley A., Stirchak E.P., Wester R.T. J. Am. Chem. Soc. 110:1988;5442.
49. Imidoesters: (a) Schenck, T. G.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2058. Xanthates:
50. (b) Auburn, P. R.; Wheland, J.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1986, 146. Nitrogroups:
51. (c) Ono, N.; Hamamoto, I.; Kamimura, A.; Kaji, A. J. Org. Chem. 1986, 51, 3734;
52. (d) Tamura, R.; Kai, Y.; Kakihama, M.; Hayashi, K.; Tsuji, M.; Nakamura, T.; Oda, D. J. Org. Chem. 1986, 51, 4375;
53. (e) Tamura, R.; Kato, M.; Saegusa, K.; Kakihama, M.; Oda, D. J. Org. Chem. 1987, 52, 4121;
54. (f) Tamura, R.; Kamimura, A.; Ono, N. Synthesis 1991, 423. Sulfones:
55. (g) Trost, B. M.; Schmuff, N. R.; Miller, M. J. J. Am. Chem. Soc. 1980, 102, 5979.
56. Lumin S., Falck J.R., Capdevila J., Karara A. Tetrahedron Lett. 33:1992;2091.
57. Tsay S., Lin L.C., Furth P.A., Shum C.C., King D.B., Yu S.F., Chen B., Hwu J.R. Synthesis. 1993;329.
58. Masuyama Y., Kagawa M., Kurusu Y. Chem. Lett. 1995;1121.
59. Hirai Y., Shibuya K., Fukuda Y., Yokoyama H., Yamaguchi S. Chem. Lett. 1997;221.
60. Stary I., Stara I.G., Kocovsky P. Tetrahedron Lett. 34:1993;179.
61. Stary I., Stara I.G., Kocovsky P. Tetrahedron. 50:1994;529.
62. Yang S.C., Chung W.H. Tetrahedron Lett. 40:1999;953.
63. Yang S.C., Hung C.W. J. Org. Chem. 64:1999;5000.
64. Yang S.C., Tsai Y.C. Organometallics. 20:2001;763.
65. Fiaud J.C., Legros J.Y. J. Org. Chem. 55:1990;4840.
66. Yamaguchi A., Shima T., Yamagishi T., Hida M. Tetrahedron Lett. 31:1990;5049.
67. Yamaguchi A., Shima T., Yamagishi T., Hida M. Tetrahedron: Asymmetry. 2:1991;663.
68. Trost B.M., Bunt R.C. J. Am. Chem. Soc. 116:1994;4089.
69. Trost B.M., Krueger A.C., Bunt R.C., Zambrano J. J. Am. Chem. Soc. 118:1996;6520.
70. Milstein D. Organometallics. 1:1982;888.
71. Scott W.J., Crisp G.T., Stille J.K. J. Am. Chem. Soc. 106:1984;4630.
72. Bäckvall J.E., Bystrom S.E., Nordberg R.E. J. Org. Chem. 49:1984;4619.
73. Scott W.J., Stille J.K. J. Am. Chem. Soc. 108:1986;3033.
74. Yang S.C., Shea F.R., Hung C.W. J. Chin. Chem. Soc. 45:1998;779.