Palladium-catalyzed amination of 2-Iodo-para-carborane

Organometallics

Volumn 26, Issue 9, 2007, Pages 2340-2347

  Beletskaya, Irina P ^a   Bregadze, Vladimir I ^b   Kabytaev, Kuanysh Z ^a   Zhigareva, Galina G ^b   Petrovskii, Pavel V ^b   Glukhov, Ivan V ^b   Starikova, Zoya A ^b  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; DERIVATIVES; ORGANOMETALLICS; PALLADIUM COMPOUNDS; X RAY DIFFRACTION;

2-IODO-P-CARBORANE; BENZIMIDAZOLE; HYDROXY DERIVATIVES; INDOLE;

CATALYST ACTIVITY;

EID: 34248327942     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0611756     Document Type: Article

References (62)

1. (a) Yang, X.; Jiang, W.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 9719.
2. (b) Mueller, J.; Base, K.; Magnera, T. F.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9721.
3. (c) Schöberl, U.; Magnera, T. E.; Harrison, R. M.; Fleischer, F.; Pflug, J. L.; Schwab, P. F. H.; Meng, X.; Lipiak, D.; Noll, B. C.; Allured, V. S.; Rudalevige, T.; Lee, S.; Michl, J. J. Am. Chem. Soc. 1997, 119, 3907.
4. (d) Schwab, P.; Levin, M. D.; Michl, J. Chem. Rev. 1999, 99, 1863.
5. (a) Murphy, D. M.; Mingos, D. M. P.; Forward, J. M. J. Mater. Chem. 1993, 3, 67.
6. (b) Murphy, D. M.; Mingos, D. M. P.; Haggitt, J. L.; Powell, H. R.; Westcott, S. A.; Marder, T. B.; Taylor, N. J.; Kanis, D. R. J. Mater. Chem. 1993, 3, 139.
7. (a) Jiang, W.; Knobler, C. B.; Curtis, C. E.; Mortimer, M. D.; Hawthorne, M. F. Inorg. Chem. 1995, 34, 3491.
8. (b) Jiang, W.; Knobler, C. B.; Hawthorne, M. F. Inorg. Chem. 1996, 35, 3056.
9. (c) Jiang, W.; Harwell, D. E.; Mortimer, M. D.; Knobler, C. B.; Hawthorne, M. F. Inorg. Chem. 1996, 35, 4355.
10. (d) Hawthorne, M. F.; Zheng, Z. Acc. Chem. Res. 1997, 30, 267.
11. (e) Bayer, M. J.; Herzog, A.; Diaz, M.; Harakas, G. A.; Lee, H.; Knobler, C. B.; Hawthorne, M. F. Chem.-Eur. J. 2003, 9, 2732.
12. (a) Colquhoun, H. M.; Herbertson, P. L.; Wade, K.; Baxter, I.; Williams, D. J. Macromolecules 1998, 31, 1694.
13. (b) Alekseyeva, E. S.; Fox, M. A.; Howard, J. A. K.; Macbride, J. A. H.; Wade, K. Appl. Organomet. Chem. 2003, 17, 499.
14. (a) Lamrani, M.; Hamasaki, R.; Mitsuishi, M.; Miyashita, T.; Yamamoto, Y. Chem. Commun. 2000, 1595.
15. (b) Tsuboya, N.; Lamrani, M.; Hamasaki, R.; Ito, M.; Mitsuishi, M.; Miyashita, T.; Yamamoto, Y. J. Mater. Chem. 2002, 12, 2701.
16. (a) Kaszynski, P.; Douglas, A. G. J. Organomet. Chem. 1999, 581, 28.
17. (b) Piecek, W.; Kaufman, J. M.; Kaszynski, P. A. Liq. Cryst. 2003, 30, 39.
18. (c) Pahomov, S.; Young, V. G.; Kaszynski, P. Inorg. Chem. 2000, 39, 2243.
19. (d) Kaszynski, P.; Pahomov, S.; Young, V. G. Collect. Czech. Chem. Commun. 2002, 67, 1061.
20. (a) Soloway, A. H.; Tjarks, W.; Barnum, B. A.; Rong, F.-G.; Barth, R. F.; Codogni, I. M.; Wilson, J. G. Chem. Rev. 1998, 98, 1515.
21. (b) Hawthorne, M. F.; Maderna, A. Chem. Rev. 1999, 99, 3421.
22. (c) Valliant, J. F.; Guenther, K. J.; King A. S. Coord. Chem. Rev. 2002, 232, 173.
23. (d) Endo, Y.; Iijima, T.; Yamakoshi, Y.; Fukasawa, H.; Miyaura, C.; Inada, M.; Kubo, A.; Itai, A. Chem. Biol. 2001, 8, 341.
24. (e) Bregadze, V. I.; Sivaev, I. B.; Glazun, S. A. Anti-Cancer Agents Med. Chem. 2006, 6, 75.
25. (a) Grimes, R. N. Carboranes; Academic Press: New York, 1970.
26. (b) Bregadze, V. I. Chem. Rev. 1992, 92, 209.
27. Marshall, W. J.; Young, R. J., Jr.; Grushin, V. V. Organometallics 2001, 20, 523.
28. (a) Zakharkin, L. I.; Kovredov, V. A.; Ol'shevskaya, V. A. Bull. Akad. Sci. USSR Div. Chem. Sci. 1981, 1775.
29. (b) Zakharkin, L. I.; Kovredov, V. A.; Ol'shevskaya, V. A.; Shaugumbekova, Z. S. J. Organomet. Chem. 1982, 226, 217.
30. (c) Zakharkin, L. I.; Ol'shevskaya, V. A. Russ. J. Gen. Chem. 1987, 57, 317.
31. (d) Kovredov, V. A.; Shaugumbekova, Z. S.; Petrovskii, P. V.; Zakharkin L. I. Russ. J. Gen. Chem. 1989, 59, 537.
32. (a) Li, J.; Logan, C. F.; Jones, M. Inorg. Chem. 1991, 30, 4866.
33. (b) Zheng, Z.; Jiang, W.; Zinn, A. A.; Knobler, C. B.; Hawthorne, M. F. Inorg. Chem. 1995, 34, 2095.
34. (c) Vinas, C.; Barbera, G.; Oliva, J. M.; Teixidor, F.; Welch, A. J.; Rosair, G. M. Inorg. Chem. 2001, 40, 6555.
35. (a) Zakharkin, L. I.; Ol'shevskaya, V. A. Synth. React. Inorg. Met.-Org. Chem. 1991, 21, 1041.
36. (b) Zakharkin, L. I.; Kovredov, A. I.; Ol'shevskaya, V. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1985, 888.
37. Eriksson, L.; Beletskaya, I. P.; Bregadze, V. I.; Sivaev, I. B.; Sjöberg, S. J. Organomet. Chem. 2002, 657, 267.
38. Eriksson, L.; Winberg, K.-J.; Claro, R. T.; Sjöberg, S. J. Org. Chem. 2003, 68, 3569.
39. (a) Beletskaya, I. P.; Bregadze, V. I.; Ivushkin, V. A.; Petrovskii, P. V.; Sivaev, I. B.; Sjöberg, S.; Zhigareva, G. G. J. Organomet. Chem. 2004, 689, 2920.
40. (b) Beletskaya, I. P.; Bregadze, V. I.; Ivushkin, V. A.; Zhigareva, G. G.; Petrovskii, P. V.; Sivaev, I. B. Russ. J. Org. Chem. 2005, 41, 1359.
41. (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
42. (b) Wolfe, J. P.; Wagaw, S.; Marcous, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
43. (a) Zakharkin L. I.; Kalinin V. N. Izv. Akad. Nauk SSSR, Ser. Khim. 1967, 2585.
44. (b) Zakharkin L. I.; Kalinin V. N.; Gedymin V. V. J. Organomet. Chem. 1969, 16, 371.
45. (c) Brattsev, V. A.; Stanko, V. I. Russ. J. Gen. Chem. 1969, 39, 2144.
46. Roscoe J. S.; Kongpricha S.; Papetti S. Inorg. Chem. 1970, 9, 1561.
47. (a) Zakharkin L. I.; Kalinin, V. N.; Gedymin, V. V. Synth. React. Inorg. Met. Org. Chem. 1973, 3, 93.
48. (b) Zakharkin, L. I.; Kalinin, V. N.; Gedymin, V. V. Russ. J. Gen. Chem. 1973, 43, 1974.
49. (c) Zakharkin, L. I.; Kalinin, V. N.; Kobelkova, N. I. Russ. J. Gen. Chem. 1980, 50, 919.
50. Beletskaya, I. P.; Davydov, D. V., Moreno-Manas, M. Tetrahedron Lett. 1998, 39, 5617.
51. Glukhov, I. V.; Lyssenko, K. A.; Korlyukov, A. A.; Antipin, M. Yu. Faraday Discuss. 2007, 203
52. Davidson, M. G.; Hibbert, T. G.; Howard, J. A. K.; Mackinnon, A.; Wade, K. Chem. Commun. 1996, 2285.
53. Morel, P.; Schaffer, P.; Vaillant, J. F. J. Organomet. Chem. 2003, 668, 25.
54. Valliant, J. F.; Schaffer, P. J. Inorg. Biochem. 2001, 85, 43.
55. Krasnov, V. P.; Levit, G. L.; Charushin, V. N.; Grishakov, A. N.; Kodess, M. I.; Kalinin, V. N.; Ol'shevskaya, V. A.; Chupakhin, O. N. Tetrahedron: Asymmetry 2002, 13, 1833.
56. Peymann, T.; Herzog, A.; Knobler, C. B.; Hawthorne, M. F. Angew. Chem., Int. Ed. 1999, 38, 1062.
57. Herzog, A.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 2001, 123, 12791.
58. Oliva, J. M.; Allan, N. L.; Schleyer, P. v. R.; Viňas, C.; Teixidor, F. J. Am. Chem. Soc. 2005, 127, 13538.
59. SAINTPlus, Data Reduction and Correction Program v. 6.01 ; Bruker AXS: Madison, WI, 1998.
60. SMART, Bruker Molecular Analysis Research Tool, v. 5.059; Bruker AXS: Madison, WI, 1998.
61. Sheldrick G. M. SADABS v.2.01, Bruker/Siemens Area Detector Absorption Correction Program; Bruker AXS: Madison, WI, 1998.
62. Sheldrick G. M. SHELXTL-97, Version 5.10; Bruker AXS Inc.: Madison, WI, 1997.