Mechanistic studies of copper(I)-catalyzed allylic amination

Journal of the American Chemical Society

Volumn 129, Issue 49, 2007, Pages 15250-15258

  Srivastava, Radhey S ^a   Tarver, Nathan R ^a   Nicholas, Kenneth M ^b  

^a UNIVERSITY OF LOUISIANA AT LAFAYETTE   (United States)

^b UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COPPER COMPOUNDS; NITROGEN COMPOUNDS; REACTION KINETICS;

MECHANISTIC STUDIES; NITROSOBENZENE; TRIGONAL PLANAR GEOMETRY;

AROMATIC COMPOUNDS;

ALKENE; ALPHA METHYLSTYRENE; COPPER; DIOXANE; HYDROXYLAMINE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENZYME ISOLATION; GEOMETRY; SPECTROSCOPY; SYNTHESIS;

EID: 37049011869     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0751072     Document Type: Article

References (77)

1. Jacobson, A. E; May, E. L.; Sargent, L. J. In Medicinal Chemistry; Burger, A., Ed.; Wiley: New York, 1970; Vol. 2, Chapter 49, pp 1330-1350.
2. Lednicer, D.; Mitscher, L. A. In Medicinal Chemistry; Burger, A., Ed.; Wiley: New York, 1984; Vol. 3, pp 116, 190.
3. Comer, W. T.; Opomoll, A. W. In Medicinal Chemistry; Burger, A., Ed.; Wiley: New York, 1970; Vol. 2, pp 1019-1064.
4. Review: Ryder, N. S.; Stuetz, A.; Nussbaumer, P.ACS Symp. Ser. 1992, 6497, 192-204.
5. Berdy, J.; Aszalos, A.; Bostian, M.; McNitt, K. L. Handbook of Antibiotic Compounds; CRC Press, Boca Raton, FL, 1928; Vol. 1.
6. Kennedy, J. F.; White, C. A. Bioactive Carbohydrates; Halstead Press: Chichester, England, 1983; pp 264-287.
7. Myers, D. In Surfactant Science and Technology; VCH: Weinheim, Germany, 1988; pp 20, 62-67.
8. Kirk-Othmer Concise Encyclopedia of Chemical Technology; Grayson, M., Ed.; Wiley and Sons: New York, 1985; pp 82-87.
9. (a) Sharpless, K. B.; Hori, T. J. Org. Chem. 1976, 41, 176.
10. (b) Kresze, G.; Braxmeier, H.; Munsterer, H. Org. Synth. 1987, 65, 159.
11. (c) Katz, T. J.; Shi, S. J. Org. Chem. 1994, 59, 8297.
12. (a) Sharpless, K. B.; Hori, T.; Truesdale, L. K.; Dietrich, C. O. J. Am. Chem. Soc. 1976, 98, 269.
13. (b) Bruncko, M.; Khuong, T. A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 454.
14. Brimble, M. A.; Heathcock, C. H. J. Org. Chem. 1993, 58, 5261.
15. Leblanc, Y.; Zamboni, R.; Bernstein, M. A. J. Org. Chem. 1991, 56, 1971.
16. Keck, G. E.; Webb, R. R.; Yates, J .B. Tetrahedron 1981, 37, 4007.
17. Knight, G. T. Chem. Commun. 1970, 1016.
18. Bank, R. E.; Hazeldine R. N.; Miller, P. J. Tetrahedron Lett. 1970, 4417.
19. Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc. 1991, 113, 3526.
20. Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673.
21. Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104.
22. Kolb, H. C.; Sharpless, K. B. Transition Met. Org. Synth. 1998, 2, 243.
23. Mueller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
24. Katsuki, T. Comp. Coord. Chem. 2 2004, 9, 207.
25. Jorgensen, K. A. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Chapter 1, p 1-35.
26. (a) Srivastava, A.; Ma, Y.; Pankayatselvan, R.; Dinges, W.; Nicholas, K. M. J. Chem. Soc., Chem. Commun. 1992, 853.
27. (b) Srivastava, R. S.; Nicholas, K. M. J. Org. Chem. 1994, 59, 5365.
28. (a) Srivastava, R. S.; Nicholas, K. M. Tetrahedon Lett. 1994, 35, 8739.
29. (b) Srivastava, R. S.; Khan, M. A.; Nicholas, K. M. J. Am. Chem. Soc. 1996, 118, 3311.
30. (c) Srivastava, R. S.; Nicholas, K. M. J. Am. Chem. Soc. 1997, 119, 3302.
31. (d) Singh, S.; Nicholas, K. M. Synth. Commun. 2001, 31, 3087.
32. Johannsen, M.; Jorgensen, K. A. J. Org. Chem. 1994, 59, 214.
33. Srivastava, R. S.; Nicholas, K. M. Chem. Commun. 1998, 2705.
34. Kolel-Veetil, M.; Khan, M. A.; Nicholas, K. M. Organometallics, 2000, 19, 3754.
35. Srivastava, R. S.; Nicholas, K. M. Tetrahedron Lett. 2002, 43, 931-934.
36. Cenini, S.; Ragaini, F.; Tollari, S.; Paone, D. J. Am. Chem. Soc. 1996, 118, 11964.
37. Ragaini, F.; Cenini, S.; Tollari, S.; Tummolillo, G.; Beltrami, R. Organometallics 1999, 18, 928.
38. Srivastava, R. S.; Nicholas, K. M. Chem. Commun. 1996, 2335.
39. Hogan, G. A.; Gallo, A. A.; Nicholas, K. M.; Srivastava, R. S. Tetrahedron Lett. 2002, 43, 9505.
40. Ho, C.-M.; Lau, T.-C. New J. Chem. 2000, 24, 859.
41. Srivastava, R. S.; Khan, M. A.; Nicholas, K. M. J. Am. Chem. Soc. 2005, 127, 7278.
42. Yamamoto, Y.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 4128.
43. Momiyama, N.; Yamamoto, H. Angew. Chem. Int. Ed. 2002, 41, 2986.
44. Momiyama, N.; Yamamoto, H. Org. Lett. 2002, 4, 3579.
45. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038.
46. Kamm, O. Org. Synth. 1925, 4, 57
47. Volger, U. Rec. Trav. Chim. Pays-Bas 1967, 86, 677.
48. Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476.
49. Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556.
50. Snider, B. Acc. Chem. Res. 1980, 13, 426.
51. Adam, W.; Bottke, N.; Krebs, O. Org. Lett. 2000, 2, 3293.
52. Ensley, H. E.; Mahadevan, S. Tetrahedron Lett. 1998, 3255.
53. Dang, H.-S.; Keck, G. E.; Webb, R. R.; Yates, J. B. Tetrahedron 1981, 37, 4007.
54. Banks, R. E.; Hazeldine, R. N.; Miller, P. J. Tetrahedron Lett. 1970, 4417.
55. Motherwell, W.; Roberts, J. S. Chem. Commun. 1972, 329.
56. Taylor, E. C.; Tseng, C.-P.; Rampal, J. B. J. Org. Chem. 1982, 47, 552.
57. Oikawa, E.; Tsubaki, S. Bull. Chem. Soc. Jpn. 1973, 46, 1819.
58. 3 complexes display nearly ideal trigonal planar geometries: Kappenstein, C.; Hugel, R. P. Inorg. Chem. 1978, 17, 1945.
59. Eller, P. G.; Corfield, P. W. R. Chem. Commun. 1971, 105.
60. Gruf, E. S.; Koch, S. A. J. Am. Chem. Soc. 1990, 112, 1245.
61. A few examples with significant distortions towards Y- or T-shapes have been reported: Coucouvanis, D.; Murphy, C. N.; Kanodia, S. K. Inorg. Chem. 1980, 19, 2993.
62. Gruf, E. S.; Koch, S. A. J. Am. Chem. Soc. 1989, 111, 8762.
63. Lewin, A. H.; Michl, R. J. Chem. Commun. 1972, 661.
64. Riehl, J. F.; El-Idrissi, R.; Jean, Y.; Pelissier, M. New J. Chem. 1991, 15, 239.
65. Talberg, H. J. Acta Chem. Scand. A 1977, 31, 743.
66. Salomon, R. G.; Kochi, J. K. J. Am. Chem. Soc. 1973, 95, 1889. Doyle, G.;
67. Eriksen, K. A.; Engen Van, D. Organometallics, 1985, 4, 830.
68. Wathen, S. P.; Czarnik, A. W. J. Org. Chem. 1992, 57, 6129.
69. Matsuguma, H. J.; Audrieth, L. F. J. Inorg. Nucl. Chem. 1959, 12, 186.
70. Srivastava, R. S. Tetrahedron Lett. 2003, 44, 3271.
71. Cundari, T. R.; Deng, J. J. Chem. Inform. Comp. Sci. 1999, 39, 376.
72. Cundari, T. R.; Deng, J.; Fu, W. Int. J. Quantum Chem. 2000, 77, 421.
73. Ball, D. M.; Buda, C.; Gillespie, A. M.; White, D. P.; Cundari, T. R. Inorg. Chem. 2002, 41, 152.
74. (a) Liepins, V.; Backvall, J.-E. Eur. J. Org. Chem. 2002, 21, 3527.
75. (b) Kondo, J.; Inoue, A.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 2002, 43, 2399.
76. (c) Levisalles, J.; Rudler-Chauvin, M.; Rudler, H. J. Organomet. Chem. 1977, 136, 103.
77. (d) Yamanaka, M.; Kato, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 6287.