Nitrosoarene-Cu(I) complexes are intermediates in copper-catalyzed allylic amination

Journal of the American Chemical Society

Volumn 127, Issue 20, 2005, Pages 7278-7279

  Srivastava, Radhey S ^a   Khan, Masood A ^b   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

COPPER DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; COMPLEX FORMATION; CRYSTALLIZATION; MOLECULAR INTERACTION; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 19744376905     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044093m     Document Type: Article

References (51)

1. For reviews, see: (a) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673.
2. (b) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104.
3. (c) Kolb, H. C.; Sharpless, K. B. Transition Met. Org. Synth. 1998, 2, 243.
4. (d) Mueller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
5. (e) Katsuki, T. Comput. Coord. Chem. 11 2004, 9, 207.
6. Jorgensen, K. A. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Chapter 1, pp 1-35.
7. (a) Srivastava, A.; Ma, Y.; Pankayatselvan, R.; Dinges, W.; Nicholas, K. M. Chem. Commun. 1992, 853.
8. (h) Srivastava, R. S.; Nicholas, K. M. J. Org. Chem. 1994, 59, 5365.
9. (a) Srivastava, R. S.; Nicholas, K. M. Tetrahedon Lett. 1994, 35, 8739.
10. (b) Srivastava, R. S.; Khan, M. A.; Nicholas, K. M. J. Am. Chem. Soc. 1996, 118, 3311.
11. (c) Srivastava, R. S.; Nicholas, K. M. J. Am. Chem. Soc. 1997, 119, 3302.
12. (d) Singh, S.; Nicholas, K. M. Synth. Commun. 2001, 31, 3087.
13. Johannsen, M.; Jorgenson, K. A. J. Org. Chem. 1994, 59, 214.
14. Hogan, G. A.; Gallo, A. A.; Nicholas, K. M.; Srivastava, R. S. Tetrahedron Lett. 2002, 43, 9505.
15. Ho, C.-M.; Lau, T.-C. New J. Chem. 2000, 24, 859.
16. (a) Srivastava, R. S.; Nicholas, K. M. Chem. Commun. 1998, 2705.
17. (b) Kolel-Veetil, M.; Khan, M. A.; Nicholas, K. M. Organometallics 2000, 19, 3754.
18. (c) Srivastava, R. S.; Kolel-Veetil, M. K.; Nicholas, K. M. Tetrahedron Lett. 2002, 43, 931.
19. (d) Cenini, S.; Ragaini, F.; Tollari, S.; Paone, D. J. Am. Chem. Soc. 1996, 118, 11964.
20. (c) Ragaini, F.; Cenini, S.; Tollari, S.; Tummolillo, G.; Beltrami, R. Orgametallics 1999, 18, 928.
21. Srivastava, R. S.; Nicholas, K. M. Chem. Commun. 1996, 2335.
22. (a) Adam, W.; Bottke, N.; Krebs, O. Org. Lett. 2000, 2, 3293.
23. (b) Ensley, H. E.; Mahadevan, S. Tetrahedron Lett. 1998, 3255.
24. (c) Dang, H.-S.; Keck, G. E.; Webb, R. R.; Yates, J. B. Tetrahedron 1981, 37, 4007.
25. (d) Banks, R. E.; Hazeldine, R. N.; Miller, P. J. Tetrahedron Lett. 1970, 4417.
26. (e) Motherwell, W.; Roberts, J. S. Chem. Commun. 1972, 329.
27. Yamamoto, Y.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 4128.
28. (a) Momiyama, N.; Yamamoto, H. Angew. Chem., Int. Ed. 2002, 41, 2986.
29. (b) Momiyama, N.; Yamamoto, H. Org. Lett. 2002, 4, 3579.
30. (c) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038.
31. Preparative and characterizational data for new compounds are provided in the Supporting Information.
32. 3 complexes display nearly ideal trigonal planar geometries: (a) Kappenstein, C.; Hugel, R. P. Inorg. Chem. 1978, 17, 1945.
33. (b) Eller, P. G.; Corfield, P. W. R. Chem. Commun. 1971, 105.
34. (c) Gruf, E. S.; Koch, S. A. J. Am. Chem. Soc. 1990, 112, 1245.
35. A few distorted toward Y- or T-shapes have been reported: (d) Coucouvanis, D.; Murphy, C. N.; Kanodia, S. K. Inorg. Chem. 1980, 19, 2993.
36. (e) Gruf, E. S.; Koch, S. A., Am. Chem. Soc. 1989, 111, 8762.
37. (f) Lewin, A. H.; Michl, R. J. Chem. Commun. 1972, 661.
38. Riehl, J. F.; El-Idrissi, R.; Jean, Y.; Pelissier, M. New. J. Chem. 1991, 15, 239.
39. Talberg, H. J. Acta Chem. Scand. A 1977, 31, 743.
40. (a) Lee, J.; Chen, L.; West, A. H.; Richter-Addo, G. B. Chem. Rev. 2002, 102, 1019.
41. (b) Popp, C. J.; Ragsdale, R. O. Inorg. Chem. 1968, 7, 1845.
42. Yield based on the stoichiometry 2 Cu(I) + PhNO + AMS → 3.
43. (a) Taylor, E. C.; Tseng, C.-P.; Rampal, J. B. J. Org. Chem. 1982, 47, 552.
44. (b) Oikawa, E.; Tsubaki, S. Bull. Chem. Soc. Jpn. 1973, 46, 1819.
45. Redox disproportionation of hydroxylamines by Cu(I,II): (a) Wathen, S. P.; Czarnik, A. W. J. Org. Chem. 1992, 57, 6129.
46. (b) Matsuguma, H. J.; Audrieth, L. F. J. Inorg. Nucl. Chem. 1959, 12, 186.
47. (c) Srivastava, R. S. Tetrahedron Lett. 2003, 44, 3271.
48. The active N-transfer agent 1 could also have L = dioxane and/or olefin. The apparent N-centered, enophilicity of 1 parallels that found in some nitrosoaldol reactions proposed to involve Ag(1)-ArNO complexes but contrasts with the O-based reactivity of others (ref 12) and with the N-O-centered reactivity in Cu(I)-catalyzed hetero-Diels-Alder reactions (ref 11).
49. (a) Cundari, T. R.; Deng, J. J. Chem. Inform. Comput. Sci. 1999, 39, 376.
50. (b) Cundari, T. R.; Deng, J.; Fu, W. Int. J. Quantum Chem. 2000, 77, 421.
51. (c) Ball, D. M.; Buda, C.; Gillespie, A. M.; White, D. P.; Cundari, T. R. Inorg. Chem. 2002, 41, 152.