Reactivity of the bis(dihydrogen) complex [RuH2(η2-H2)2 (PCy3)2] toward N-heteroaromatic compounds. Regioselective hydrogenation of acridine to 1,2,3,4,5,6,7,8-octahydroacridine

Organometallics

Volumn 22, Issue 8, 2003, Pages 1630-1637

  Borowski, Andrzej F ^a,b   Sabo Etienne, Sylviane ^b   Donnadieu, Bruno ^b   Chaudret, Bruno ^b  

^a POLISH ACADEMY OF SCIENCES   (Poland)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; COMPLEXATION; HYDROGENATION; NITROGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTONS; X RAY CRYSTALLOGRAPHY;

ACRIDINE; ISOQUINOLINE; PROTONATION; PYRIDINE; PYRROLE; QUINOLINE; REGIOSELECTIVE HYDROGENATION;

RUTHENIUM COMPOUNDS;

EID: 0038303167     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020995p     Document Type: Article

References (67)

1. Girgis, M. J.; Gates, B. C. Ind. Eng. Chem. Res. 1991, 30, 2021.
2. Weller, K. J.; Fox, P. A.; Gray, S. D.; Wigley, D. E. Polyhedron 1997, 16, 3139 and refrences therein.
3. March, J. Advanced Organic Chemistry: Mechanisms and Structure, 4th ed.; Wiley: New York, 1992.
4. Baralt, E.; Smith, S. J.; Hurwitz, J.; Horváth, I. T.; Fish, R. H. J. Am. Chem. Soc. 1992, 114, 5187.
5. (a) Topsøe, H.; Clausen, B. S.; Massoth, F. E. Hydrotreating Catalysis. In Catalysis: Science and Technology; Anderson, J. R., Boudart, M., Eds.; Springer-Verlag: Berlin, Heidelberg, 1996; Vol. 11.
6. (b) Satterfield, C. N. Heterogeneous Catalysis in Industrial Practice; McGraw-Hill: New York, 1991; p. 378.
7. Angelici, R. J. Polyhedron 1997, 116, 3037 and references therein.
8. Kvietok, F.; Allured, V.; Carperos, V.; Rakowski DuBois, M. Organometallics 1994, 13, 60.
9. (a) Vicic, D. A.; Jones, W. D. Organometallics 1999, 18, 134.
10. (b) Morikita, T.; Hirano, M.; Sasaki, A.; Komiya, S. Inorg. Chim. Acta 1999, 291, 341.
11. (c) Werner, H.; Hoerlin, G.; Jones, W. D. J. Organomet. Chem. 1998, 562, 45.
12. Chisholm, M. H. Polyhedron 1997, 16, 3071.
13. (a) McComas, C. C.; Ziller, J. W.; Van Vranken, D. L. Organometallics 2000, 19, 2853.
14. (b) Sculte, J. L.; Laschat, S.; Kotila, S.; Hecht, J.; Fröhlich, R.; Wibbeling, B. Heterocycles 1996, 43, 2713.
15. (c) Joachim, J. E.; Apostolidis, C.; Kanellakopulos, B.; Meyer, D.; Raptis, K.; Rebizant, J.; Ziegler, M. L. J. Organomet. Chem. 1994, 476, 77.
16. (d) Laschat, S.; Noe, R.; Riedel, M.; Krüger, C. Organometallics 1993, 12, 3738.
17. (e) Myers, W. H.; Koontz, J. I.; Harman, W. D. J. Am. Chem. Soc. 1992, 114, 5684.
18. (f) Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1991, 113, 6682.
19. (g) Glueck, D. S.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1991, 113, 6682.
20. (h) Cordone, R.; Harman, W. D.; Taube, H. J. Am. Chem. Soc. 1991, 113, 5969.
21. (i) Chaudret, B.; Jalon, F.; Perez-Manrique, M.; Lahoz, F. J.; Plou, F. J.; Sanchez-Delgado, R. New J. Chem. 1990, 14, 331.
22. (j) Kershner, D. L.; Rheingold, A. L.; Basolo, F. Organometallics 1987, 6, 196.
23. (k) Pyshnograeva, N. I.; Setkina, V. N.; Adrianow, V. G.; Struchov, Yu. T.; Kursanov, D. N. J. Organomet. Chem. 1980, 186, 331.
24. Esteruelas, M. A.; Oro, L. A. Chem. Rev. 1998, 98, 577.
25. (a) Sabo-Etienne, S.; Chaudret, B. Coord. Chem. Rev. 1998, 170-180, 381.
26. (b) Borowski, A. F.; Donnadieau, B.; Daran, J.-C.; Sabo-Etienne, S.; Chaudret, B. Chem. Commun. 2000, 543, 1697.
27. Borowski, A. F.; Sabo-Etienne, S.; Chaudret, B. J. Mol. Catal. A: Chem. 2001, 174, 69.
28. Toner, A. J.; Donnadieu, B.; Sabo-Etienne, S.; Chaudret, B.; Sava, X.; Mathey, F.; Le Floch, P. Inorg. Chem. 2001, 40, 3034.
29. (a) Fish, R. H.; Baralt, E.; Smith, S. J. Organometallics 1991, 10, 54.
30. (b) Borowski, A. F.; Cole-Hamilton, D. J. Polyhedron 1993, 12, 1757.
31. (c) Studer, M.; Wedemayer-Exl, C.; Spindler, F.; Baser, H. U. Monatsh. Chem. 2000, 131, 1335.
32. Fish, R. H.; Kim, H. S.; Babin, J. E.; Adams, R. D. Organometallics 1988, 7, 2250.
33. (a) Rosales, M.; Navarro, J.; Sanchez, L.; Gonzalez, A.; Alvorado, Y.; Rubio, R.; De La Cruz, C.; Ramajkina, T. Transition Met. Chem. 1996, 21, 11.
34. (b) Rosales, M.; Alvorado, Y.; Boves, M.; Rubio, R.; Soscún, H. Transition Met. Chem. 1995, 20, 246.
35. Sanchez-Delgado, R. A.; Rondon, D.; Andriollo, A.; Herrera, V.; Martin, G.; Chaudret, B. Organometallics 1993, 12, 4291.
36. (a) Albright, J. O.; Datta, S.; Dezube, B.; Kouba, J. K.; Marynick, D. S.; Wreford. S. S.; Foxman, B. M. J. Am. Chem. Soc. 1979, 101. 611.
37. (b) Leong, V. S.; Cooper, N. J. Organometallics 1988, 7, 2058.
38. (c) Thompson, R. L.; Lee, R.; Rheingold, A. L.; Cooper, N. J. Organomatallics 1991, 10, 1657.
39. (d) Bennett, M. A.; Lu, Z.; Wang, X.; Brown, M.; Hockless, D. C. R. J. Am. Chem. Soc. 1998, 120, 10409.
40. Fish, R. H.; Kim, H. S.; Fong, R. H. Organometallics 1991, 10, 770.
41. (a) Guari, Y.; Sabo Etienne, S.; Chaudret, B. J. Am. Chem. Soc. 1998, 120, 4228.
42. (b) Toner, A. J.; Grundemann, S.; Clot, E.; Limbach, H.-H.; Donnadieu, B.; Sabo-Etienne, S.; Chaudret, B. J. Am. Chem. Soc. 2000, 122, 6777.
43. Grundemann, S.; Toner, A.; Matthes, J.; Guari, Y.; Donnadieu, B.; Sabo-Etienne, S.; Clot, E.; Limbach, H.-H.; Chaudret, B. To be submitted for publication.
44. Chin, C. S.; Park, Y.; Lee, B. Catal. Lett. 1995, 31, 239.
45. (a) Jia, G.; Lough, A. J.; Morris, R. H. Organometallics 1992, 11, 161.
46. (b) Chinn, M. S.; Heinekey, D. M. J. Am. Chem. Soc. 1990, 112, 5166.
47. (a) Sloufova, I.; Slouf, M. Acta Crystallogr., Sect. C: Cryst. Commun. 2000, 56, 1312.
48. (b) Sloufova. I.; Slouf. M. Acta Crystallogr., Sect. C: Cryst. Commun. 2001, 57, 248.
49. Phillips, D. C.; Ahmed, F. R.; Barnes, W. H. Acta Crystallogr. 1960, 13, 365.
50. (a) Fish, R. H.; Thormodsen, A. D.; Cremer, G. A. J. Am. Chem. Soc. 1984, 104, 5234
51. (b) Fish, R. H.; Tan, J. L.; Thormodsen, A. D. J. Org. Chem. 1984, 49, 4500.
52. Lee, C.; Steele, B. R.; Sutherland, R. G. J. Organomet. Chem. 1980, 186, 265.
53. Feder, H. M.; Halpern, J. J. Am. Chem. Soc. 1975, 97, 7186.
54. Sakanishi, K.; Ohira, M.; Mochida, I. J. Chem. Soc., Perkin Trans. 1988, 1769.
55. (a) Delpech, F.; Sabo-Etienne, S.; Daran, J.-C.; Chaudret, B.; Hussein, K.; Marsden, C. J.; Barthelat, J.-C. J. Am. Chem. Soc. 1999, 121, 6668.
56. (b) Atheaux, I.; Donnadieu, B.; Rodriguez, V.; Sabo-Etienne, S.; Chaudret, B.; Hussein, K.; Barthelat, J.-C. J. Am. Chem. Soc. 2000, 122, 5664.
57. (c) Delpech, F.; Mansas, J.; Leuser, H.; Sabo-Etienne, S.; Chaudret, B. Organometallics 2000, 19, 5750.
58. (d) Montiel-Palma, V.; Lumbierres, M.; Donnadieu, B.; Sabo-Etienne, S.; Chaudret, B. J. Am. Chem. Soc. 2002, 124, 5624.
59. Zhu, G.; Tanski, J. M.; Churchill, D. G.; Janak, K. E.; Parkin, G. J. Am. Chem. Soc. 2002, 124, 13658.
60. Pilato, M. L.; Catalano, V. J.; Bell, T. W. J. Org. Chem. 2001, 66. 1525.
61. (a) Anton, D. R.; Crabtree, R. H. Organometallics 1983, 2, 855.
62. (b) Morton, D.; Cole-Hamilton, D. J.; Utuk, I. D.; Paneque-Sosa, M.; López-Poveda, M. J. Chem. Soc., Dalton Trans. 1989, 489.
63. Altomare, A.; Cascarano, G.; Giacovazzo G.; Guagliardi A.; Burla M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.
64. Sheldrick, G. M. SHELX-97, Program for Crystal Structure Analysis; Universität Göttingen, Göttingen, Germany, 1998.
65. WINGX Program: Farrugia, L. J. J. Appl. Crystallogr. 1999. 32, 837.
66. ORTEP3 for Windows: Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
67. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. IV.