Cationic iridium complexes bearing imidazol-2-ylidene ligands as transfer hydrogenation catalysts

Organometallics

Volumn 20, Issue 20, 2001, Pages 4246-4252

  Hillier, Anna C ^a   Lee, Hon Man ^a   Stevens, Edwin D ^a   Nolan, Steven P ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC NITRO COMPOUND; CATIONIC IRIDIUM COMPLEXES; TRANSFER HYDROGENATION REACTIONS;

AROMATIC COMPOUNDS; CATALYSTS; HYDROGENATION; ION EXCHANGE; MOLECULAR STRUCTURE; OLEFINS; POSITIVE IONS; SUBSTRATES; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

IRIDIUM COMPOUNDS;

EID: 0035497170     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0103456     Document Type: Article

References (78)

1. Braude, E. A.; Linstead, R. P. J. Chem. Soc. 1954, 3544-3547.
2. (a) Brieger, G.; Nestrick, T. J. Chem. Rev. 1974, 74, 567-580.
3. (b) Bagnell, L.; Strauss, C. R. Chem. Commun. 1999, 287-288.
4. (a) Johnstone, R. A. W.; Wilby, A. H.; Entwhistle, I. D. Chem. Rev. 1985, 129-170.
5. (b) Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91-95.
6. (c) Zassinovitch, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051-1069.
7. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
8. (b) Noyori, R. Chem. Soc. Rev. 1989, 18, 187-208.
9. (d) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102.
10. (a) Braunstein, P.; Naud, F.; Rettig, S. J. New J. Chem. 2001, 25, 32-39.
11. (b) Braunstein, P.; Fryzuk, M. D.; Naud, F.; Rettig, S. J. J. Chem. Soc., Dalton Trans. 1999, 589-594.
12. (c) Braunstein, P.; Naud, F.; Graiff, C.; Tiripicchio, A. Chem. Commun. 2000, 897-898.
13. Hermann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1049-1067.
14. (a) Crabtree, R. H.; Felkin, H.; Morris, G. E. J. Organomet. Chem. 1977, 135, 205-215.
15. (b) Crabtree, R. H.; Morris, G. E. J. Organomet. Chem. 1977, 135, 395-403.
16. (c) Crabtree, R. H. Acc. Chem. Res. 1979, 12, 331-338.
17. (d) Crabtree, R. H.; Felkin, H.; Fillebeen-Khan, T.; Morris, G. E. J. Organomet. Chem. 1979, 168, 183-195.
18. (a) Ogo, S.; Makihara, N.; Watanabe, Y. Organometallics 1999, 18, 5470-5474.
19. (b) Tani, K.; Iseki, A.; Yamagata, T. Chem. Commun. 1999, 1821-1822.
20. (c) Tani, K.; Iseki, A.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pflatz, A. Synthesis 1999, 4, 597-602.
21. (d) Mizugaki, T.; Kanayama, Y.; Ebitani, K.; Kaneda, K. J. Org. Chem. 1998, 63, 2378-2381.
22. (e) Bianchini,C.; Peruzzini, M.; Farnetti, E.; Kaspar, J.; Graziani, M. J. Organomet. Chem. 1995, 488, 91-97 and references therein.
23. (f) Bianchini, C.; Farnetti, E.; Graziani, M.; Nardin, G.; Vacca, A.; Zanobini, F. J. Am. Chem. Soc. 1990, 112, 9190-9197.
24. (g) Felfoldi, K.; Kapocsi, I.; Bartók, M. J. Organomet. Chem. 1984, 277, 439-441.
25. (h) Farnetti, E.; Kaspar, J.; Graziani, M. J. Mol. Catal. 1990, 63, 5-13.
26. (i) Spogliarich, R.; Mestroni, G.; Graziani, M. J. Mol. Catal. 1984, 22, 309-311.
27. (j) Spogliarich, R.; Tencich, A.; Kaspar, J.; Graziani, M. J. Organomet. Chem. 1982, 240, 453-459.
28. (k) Uson, R.; Oro, L. A.; Carmona, D.; Esteruelas, M. A. Inorg. Chim. Acta 1983, 73, 275-279.
29. (l) Bianchini, C.; Glendenning, L.; Zanobini, F.; Farnetti, E.; Graziani, M.; Nagy, E. J. Mol. Catal. A: Chem. 1998, 132, 13-19.
30. (m) Fragale, C.; Gargano, M.; Rossi, M. J. Mol. Catal. 1979, 5, 65-73.
31. (n) Camus, A.; Mestroni, G.; Zassinovich G. J. Mol. Catal. 1989, 6, 231-233.
32. (o) Werner, H.; Schulz, M.; Esteruelas, M. A.; Oro, L. A. J. Organomet. Chem. 1993, 445, 261-265.
33. (p) Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010-3017.
34. (a) Regitz, M.; Angew. Chem., Int. Ed. Engl. 1996, 35, 725-728.
35. (b) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187.
36. (c) Arduengo, A. J., III; Krafczuk, R. Chem. Z. 1998, 32, 6-14.
37. (d) Dullins, J. E. L.; Suarez, P. A. Z.; Einloft, S.; de Souza, R. F.; Dupont, J.; Fischer, J.; De Cian, A. Organometallics 1998, 17, 815-819.
38. (e) Arduengo, A. J., III Acc. Chem. Res. 1999, 32, 913-921.
39. (f) Bourissou, D.; Guerret, O.; Gabbaï F. P.; Bertrand, G.; Chem. Rev. 2000, 100, 39-92.
40. Lee, H. M.; Jiang, T.; Stevens, E. D.; Nolan, S. P. Organometallics 2001, 20, 1255-1258.
41. These reactions are rather slow, and in some preparations varying amounts of the starting iridium complex can remain. In the case of IMes and IPr very small amounts of a second product, containing cod and carbene but no pyridine, were obtained. the exact composition of these compounds has not yet been fully elucidated. Additionally, there is some evidence for lability of one or more ligands in 2-4 from NMR studies on samples kept in solution for several weeks. A study imed at understanding the solution behavior of these complexes is ongoing.
42. Huang, J.; Schanz, H.-J: Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370-2375.
43. Bikrani, M.; Fidalgo, L.; Garralda, M. A. Polyhedron 1996, 15, 83-89.
44. (a) Zassinovich, G.; Bettella, R.; Mestroni, G.; Bresciani-Pahor, N.; Geremia, S.; Randaccio, L. J. Organomet. Chem. 1989, 370, 187-202.
45. (b) Zassinovich, G.; Camus, A.; Mestroni, G. J. Mol. Catal. 1980, 9, 345-347.
46. (c) Bikrani, M.; Fidalgo, L.; Garralda, M. A.; Ubide, C. J. Mol. Catal. A: Chem. 1997, 118, 47-53.
47. Bianchini, C.; Farnetti, E.; Glendenning, L.; Graziani, M.; Nardin, G.; Peruzzini, M.; Rocchini, E.; Zanobini, F. Organometallics 1995, 14, 1489-1502.
48. Farnetti, E.; Vinzi, F.; Mestroni, G. J. Mol. Catal. 1984, 24, 147-163.
49. (a) Chin, C. S.; Lee, B. J. Chem. Soc., Dalton Trans. 1991, 1323-1327.
50. (b) Chin, C. S.; Lee, S. Y.; Park, J.; Kim, S. J. Am. Chem. Soc. 1988, 110, 8244-8245.
51. (a) Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1999, 121, 3992-3999.
52. (b) Gupta, M.; Hagen, C.; Kaska, W. C.; Cramer, R. E.; Jensen, C. M. J. Am. Chem. Soc. 1997, 119, 840-841.
53. (c) Burk, M. J.; Crabtree, R. H. J. Am. Chem. Soc. 1987, 109, 8025-8032.
54. (d) Crabtree, R. H.; Mihelcic, J. M.; Quirk, J. M. J. Am. Chem. Soc. 1979, 101, 7738-7740.
55. (e) Baudry, M. J.; Ephritikine, M.; Felkin, H.; Holmes-Smith, R. J. Chem. Soc., Chem. Commun. 1983, 788-789.
56. (f) Burk, M. J.; Crabtree, R. H.; Parnel, C. P.; Urierte, R. J. Organometallics 1984, 3, 816-817.
57. (g) Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970-1973.
58. (h) Lohrenz, J. C. W.: Jacobsen, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1305-1307.
59. (i) Braunstein, P.; Chauvin, Y.; Nähring, J.; DeCian, A.; Fischer, J.; Tiripicchio, A.; Ugozzoli, F. Organometallics 1996, 14, 5551-5567.
60. (j) Fragale, C.; Gargano, M.; Rossi, M. J. Mol. Catal. 1979, 5, 65-73.
61. Mestroni, G.; Zassinoich, G.; del Bianco, C.; Camus, A. J. Mol. Catal. 1983, 18, 33-40.
62. Tani, K.; Iseki, A.; Yamagata, T. Chem. Commun. 1999, 1821-1822.
63. (a) Uematsu, U.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916-4917.
64. (b) Mao, J.; Baker, D. C. Org. Lett. 1999, 1, 841-843.
65. (c) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045-2061 and references therein.
66. (a) Wilds, A. L. Org. React. 1944, 2, 178.
67. (b) Moulton, W. N.; van Atta, R. E.; Ruch, R. R. J. Org. Chem. 1961, 26, 290.
68. (c) Shiner, V. J., Jr.; Whittaker, D. J. Am. Chem. Soc. 1969, 394.
69. (b) Snyder, C. H.; Micklus, M. J. J. Org. Chem. 1970, 35, 264.
70. (e) Casiraghi, G.; Casnati, G.; Sartori, G.; Zanafredi, G. T. J. Chem. Soc., Perkin Trans. 1980, 2, 407.
71. Yamakawa, M.; Ito, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 1466-1478.
72. (a) Wanzlick, H.-W. Angew. Chem., Int. Ed. Engl. 1962, 1, 75-80.
73. (b) Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. J. Am. Chem. Soc. 1991, 113, 361-363.
74. (c) Arduengo, A. J., III; Gamper, S. F.; Calabrese, J. C.; Davidson, F. J. J. Am. Chem. Soc. 1994, 116, 4391-4393.
75. Arduengo, A. J., III; Davidson, F. J.; Krafczyk, R.; Marshall, W. J.; Tamm, M. Organometallics 1998, 17, 3375-3382.
76. (a) van Koten, G.; Vrieze, K. Adv. Organomet. Chem. 1982, 21, 151-239 and references therein.
77. (b) Kliegman, J. M.; Barnes, R. K. Tetrahedron 1970, 26, 2555-2560.
78. Crabtree, R. H.; Morehouse, S. M. Inorg. Synth. 1986, 24, 173-176.