Synthesis, structure, and reactions of 1-fert-butyl-2-diphenylphosphino- imidazole

Inorganic Chemistry

Volumn 50, Issue 3, 2011, Pages 793-799

  Sauerbrey, Susanne ^a   Majhi, Paresh Kumar ^a   Daniels, Jörg ^a   Schnakenburg, Gregor ^a   Bmndle, Gerhard Markus ^a   Scherer, Katharina ^a   Streubel, Rainer ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79951645442     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic101122n     Document Type: Article

References (61)

1. A literature search yielded more than 500 N1 substituted, more than 100 N1-organyl, C2 substituted, less than 20 N1-organyl, C4 substituted but not a single N1-organyl, C5 substituted imidazole derivative with a phos-phanyl-or phosphoryl-substituent.
2. According to the Hantzsch and Widman nomenclature system, the imidazole ring is numbered starting from the nitrogen atom bearing the substitutent with the higher priority in such a way that the two nitrogen atoms receive the smallest possible numbers; 1 and 3.
3. Kowalska, J.; Lewdorowicz, M.; Zuberek, J.; Grudzien-Nogalska, E.; Bojarsaka, E.; Stepinski, J.; Rhoads, R. E.; Darzynkiewicz, E.; Davis, R. E.; Jemielity, J. RNA 2008, 14, 1119-1131.
4. Reddy, M. V. N.; Ravi, A. V. R; Reddy, C. S.; Raju, C. N. S. Afr. J. Chem. 2008, 61, 43-16.
5. Iddon, B.; Ngochindo, R. I. Heterocvcks 1994, 38, 2487-2568.
6. Spencer, L. P.; Altwer, R.; Wie, P.; Gelmini, L.; Gauld, J.; Stephan, D. W. Organometallics 2003, 22, 3841-3854.
7. Grotjahn, D. B.; Larsen, C. R.; Gustafson, J. L.; Nair, R.; Sharma, A. J. Am. Chem. Soc. 2007, 129, 9592-9593.
8. Grotjahn, D. B. Dalton Trans. 2008, 6497-6508.
9. Erdogan, G.; Grotjahn, D. B. J. Am. Chem. Soc. 2009, 131, 10354.
10. Grotjahn, D. B. Pure Appl. Chem. 2010, 82, 635-647.
11. Singer, R. A.; Tom, N. J.; Frost, H. N.; Simon, W. M. Tetrahedron Lett. 2004, 45, 4715-4718.
12. Harkal, S.; Rataboul, F.; Zapf, A.; Fuhrmann, C.; Riermeier, T.; Monsees, A.; Beller, M. Adv. Synth. Catal. 2004, 346, 1742-1748.
13. Tejel, C.; Bravi, R.; Cmano, M. A.; Oro, L. A.; Bordonaba, M.; Graiff, C.; Tiripicchio, A.; Burini, A. Organometallics 2000, 19, 3115-3119.
14. Grotjahn, D. B.; Incarvito, C. D.; Rheingold, A. L. Angew. Chem. 2001, 113, 4002-4005.
15. Grotjahn, D. B.; Incarvito, C. D.; Rheingold, A. L. Angew. Chem., Int. Ed. 2001, 40, 3884-3887.
16. Grotjahn, D. B. Chem.-Eur. J. 2005, 11, 7146-7153.
17. Grotjahn, D. B.; Miranda-Soto, V.; Kragulj, E. J.; Lev, D. A.; Erdogan, G.; Zeng, X.; Cooksy, A. L. J. Am. Chem. Soc. 2008, 130, 20-21.
18. Grotjahn, D. B.; Kragulj, E. J.; Zeinalipour-Yazdi, C. D.; Miranda-Soto, V.; Lev, D. A.; Cooksy, A. L. J. Am. Chem. Soc. 2008, 130, 10860-10861.
19. Slebocka-Tilk, H.; Cocho, J. L.; Frachman, Z.; Brown, R. S. J. Am. Chem. Soc. 1984, 106, 2421-2431.
20. Burini, A.; Pietroni, B. R.; Galassi, R.; Valle, G.; Calogero, S. Inorg. Chim. Acta 1995, 229, 299-305.
21. Tejel, C.; Ciriano, M. A.; Bravi, R.; Oro, L. A.; Graiff, C.; Galassi, R.; Burini, A. Inorg. Chim. Acta 2003, 347, 129-136.
22. Kanazawa, C.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2006, 128, 10662-10663.
23. Huang, W.; Yuan, C. Synthesis 1996, 511-513.
24. Bartlett, P. A.; Hunt, J. T.; Adams, J. L.; Gehret, J.-C. E. Bioorg. Chem. 1978, 7, 421-436.
25. Berens, U. PCT Int. Appl. WO 200331456/A2, 2003.
26. Iddon, B. Heterocycles 1985, 23, 417-443.
27. Iddon, B.; Lim, B. L. J. Chem. Soc., Perkin Trans. 1 1983, 279-283 and 735-739.
28. Iddon, B.; Khan, N. Tetrahedron Lett. 1986, 27, 1635-1638.
29. Iddon, B.; Khan, N.; Lim, B. L. J. Chem. Soc., Perkin Trans 1. 1987, 1437-1443, 1445-1451, and 1453-1455.
30. Carver, D. S.; Lindell, S. D.; Saville-Stones, E. A. Tetrahedron 1997, 53, 14481-14496.
31. Saxon, E.; Armstrong, J. I.; Bertozzi, C. R. Org. Lett. 2000, 2, 2141-2143.
32. Komarov, I. V.; Strizhak, A. V.; Kornilov, M. Y.; Kostyuk, A. N.; Tolmachev, A. A. Synth Commun. 1998, 28, 2355-2370.
33. Tolmachev, A. A.; Yurchenko, A. A.; Merculov, A. S.; Semenova, M. G.; Zarudnitskii, E. V.; Ivanov, V. V.; Pinchuk, A. M. Heteroat. Chem. 1999, 10, 585-597.
34. Grotjahn, D. B.; Gong, Y.; Zakharov, L.; Golen, J. A.; Rheingold, A. L. J. Am. Chem. Soc. 2006, 128, 438-153
35. Cingolani, E. A.; Martini, D.; Pettinari, C.; Skeldon, B. W.; White, A. H. Inorg. Chim. Acta 2006, 359, 2183-2193.
36. Hanaoka, H.; Yamamoto, M.; Goto, F.; Jpn. Kokai Tokkyo Koho JP 2008247745/A, 2008.
37. Almaraz, E.; Foley, W. S.; Denny, J. A.; Reibenspies, J. H.; Golden, M. L.; Darensbourg, M. Y. Inorg. Chem. 2009, 48, 5288-5295.
38. Graf, F.; Hupfer, L.; U. S. Patent 4,450,277, 1984.
39. Chadwick, D. J.; Ngochindo, R. I. J. Chem Soc., Perkin Trans. I 1984, 481-186.
40. Yoshida, Y.; Baba, O.; Larriba, C.; Saito, G. J. Phys. Chem. B 2007, 111, 12204-12210.
41. Ishikawa, T. Superbases in Organic Synthesis; John Wiley and Sons: West Sussex, 2009.
42. Schmidpeter, A. Phosphorus, Sulfur Silicon Relat. Elem. 1985, 22, 323-325.
43. Hunter, D.; Michie, J. K.; Miller, J. A.; Stewart, W. Phosphorus, Sulfur Silicon Relat. Elem. 1981, 10, 267-270.
44. Moedritzer, K.; Maier, L.; Groenweghe, L. C. D. J. Chem. Eng. Data 1962, 7, 308-310.
45. Al-Farhan, K. A. J. Crystallogr. Spectrosc. Res. 1992, 22, 687-689.
46. Codding, P. W.; Kerr, K. A. Acta Crystallogr. 1978, B34, 3785-3787.
47. Codding, P. W.; Kerr, K. A. Acta Crystallogr. 1979, B35, 1261-1263.
48. For comparison of the 31P NMR data of methyldiorganylphospho-nium salts see: Choi, P. C.; Morris, J. H.; J. Chem. Soc. Dalton Trans. 2119-2125
49. Yamamoto, Y.; Kanda, Z.; Bull. Chem. Soc. Jpn. 1980, 53, 3436-3438.
50. Braunstein, P.; Bender, R.; Jud, J. Inorg. Synth. 1989, 26, 341-350.
51. Nishide, K.; Ito, S.; Yoshifuji, M. J. Organomet. Chem. 2003, 682, 79-84.
52. Grundy, J.; Coles, M. P.; Hitchcock, P. B. Dalton Trans. 2003, 2573-2577.
53. Kormarov, I. V.; Kornilov, M. Y.; Tolmachev, A. A.; Rusanov, E. B.; Chernega, A. N. Tetrahedron 1995, 51, 11271-11280.
54. Grotjahn, D. B.; Gong, Y.; diPasquale, A. G.; Zakharov, L. N.; Rheingold, A. L. Organometallics 2006, 25, 5693-5695.
55. Four membered chelate complexes involving C2-phosphorus substituted imidazole derivatives are known for ruthenium54.55 and palladium.56-58
56. Caballero, A.; Jalon, F. A.; Manzano, B. R.; Espino, G.; Perez-Manrique, M.; Mucientes, A.; Poblete, F. J.; Maestro, M. Organometallics 2004, 23, 5694-5706.
57. Espino, G.; Jalon, F. A.; Maestro, M.; Manzano, B. R.; Perez-Manrique, M.; Bacigalupe, A. C. Eur. J. Inorg. Chem. 2004, 12, 2542-2552.
58. Grotjahn, D. B.; Gong, Y.; Zakharov, L.; Golen, J. A.; Rheingold, A. L. J. Am. Chem. Soc. 2006, 128, 438-453.
59. Torborg, C.; Huang, J.; Schulz, T.; Schaeffner, B.; Zapf, A.; Spannenberg, A.; Boerner, A.; Beller, M. Chem.-Eur. J. 2009, 15, 1329-1336.
60. Sergev, A. G.; Schulz, T.; Torborg, C.; Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem. 2009, 121, 7731-7735.
61. Sergev, A. G.; Schulz, T.; Torborg, C.; Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 7595-7599.