Catalytic amidation of 9-iodo-m-carborane and 2-iodo-p-carborane at a boron atom

Organometallics

Volumn 27, Issue 22, 2008, Pages 5937-5942

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

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

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

Author keywords

[No Author keywords available]

Indexed keywords

BORON; BORON COMPOUNDS; ETHERS; PALLADIUM;

AMIDATION; BINAPHTHYL; BORON ATOMS; CARBORANE; CARBORANYL; DIPHENYLPHOSPHINO; HIGH YIELDS; PYRROLIDINONE; X-RAY DIFFRACTIONS;

AMIDES;

EID: 57049110451     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800635d     Document Type: Article

References (48)

1. 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. (a) Zakharkin, L. I.; Kovredov, V. A.; Ol'shevskaya, V. A.; Shaugumbekova, Z. S. J. Organomet. Chem. 1982, 226, 217.
28. (b) Vinas, C.; Barbera, G.; Oliva, J. M.; Teixidor, F.; Welch, A. J.; Rosair, G. M. Inorg. Chem. 2001, 40, 6555.
29. (c) Jiang, W.; Harwell, D. E.; Mortimer, M. D.; Knobler, C. B.; Hawthorne, M. F. Inorg. Chem. 1996, 35, 4355.
30. (d) Li, J.; Logan, C. F.; Jones, M. Inorg. Chem. 1991, 30, 4866.
31. (e) Zheng, Z.; Jiang, W.; Zinn, A. A.; Knobler, C. B.; Hawthorne, M. F. Inorg. Chem. 1995, 34, 2095.
32. (f) Eriksson, L.; Beletskaya, I. P.; Bregadze, V. I.; Sivaev, I. B.; Sjöberg, S. J. Organomet. Chem. 2002, 657, 267.
33. Negishi, E., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley: New York, 2002.
34. Marshall, W. J.; Young, R. J., Jr.; Grushin, V. V. Organometallics 2001, 20, 523.
35. Viňas, C.; Barbera, G.; Oliva, J. M.; Teixidor, F.; Welch, A. J.; Rosair, G. M. Inorg. Chem. 2001, 40, 6555.
36. (a) Fujita, K.; Yamashita, M.; Puschmann, F.; Alvarez-Falcon, M. M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 9044.
37. (b) Ikawa, T.; Barder, T. E.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 13001.
38. Beletskaya, I. P.; Bregadze, V. I.; Kabytaev, K. Z.; Zhigareva, G. G.; Petrovskii, P. V.; Glukhov, I. V.; Starikova, Z. A. Organometallics 2007, 26, 2340.
39. Miyaura, N., Ed. Cross-coupling Reactions, A Practical Guide; Springer: Berlin, Germany, 2002; Top. Curr. Chem. 219.
40. 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.
41. (a) Grushin, V. V.; Bregadze, V. I.; Kalinin, V. N. In Journal of Organometallic Chemistry Library, Organometallic Chemistry Reviews; Davies, A. G., Fisher, E. O., Reutov, O. A., Eds.; Elsevier: Amsterdam, 1988; Vol. 20, pp 1-68.
42. (b) Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 1, pp 217-255.
43. (c) Comprehensive Organometallic Chemistry III; Mingos, D. M. P., Crabtree, R. H., Eds.; Elsevier: Amsterdam, 2007; Vol. 3, pp 49-112.
44. Kalinin, V. N.; Kobel'kova, N. I.; Krasnokutskaya, E. V.; Zakharkin, L. I. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1983, 1084.
45. SAINTPlus, Data Reduction and Correction Program, v. 6.01; Bruker AXS, Madison, WI, 1998.
46. SMART, Bruker Molecular Analysis Research Tool, v. 5.059; Bruker AXS, Madison, WI, 1998.
47. Sheldrick, G. M. SADABS, Bruker/Siemens Area Detector Absorption Correction Program v.2.01; Bruker AXS, Madison, WI, 1998.
48. Sheldrick, G. M. SHELXTL-97, Version 5.10; Bruker AXS Inc., Madison, WI, 1997.