Indium and ruthenium complexes with chelating N-heterocyclic carbenes: Efficient catalysts for transfer hydrogenation, β-alkylation of alcohols, and N-alkylation of amines

Organometallics

Volumn 28, Issue 1, 2009, Pages 321-325

  Gnanamgari, Dinakar ^a   Sauer, Effiette L O ^a   Schley, Nathan D ^a   Butler, Chase ^a   Incarvito, Christopher D ^a   Crabtree, Robert H ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AIR STABLES; EFFICIENT CATALYSTS; FUNCTIONALIZED N-HETEROCYCLIC CARBENE; IR COMPLEXES; N ALKYLATIONS; N-HETEROCYCLIC CARBENES; NMR SPECTROSCOPIES; PRIMARY ALCOHOLS; RU COMPLEXES; RUTHENIUM COMPLEXES; SECONDARY ALCOHOLS; SINGLE-CRYSTAL X-RAY DIFFRACTIONS; TRANSFER HYDROGENATIONS;

ALKYLATION; AMINATION; AMINES; CHELATION; HYDROCARBONS; HYDROGENATION; IRIDIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RUTHENIUM; SYNTHESIS (CHEMICAL);

RUTHENIUM COMPOUNDS;

EID: 61849124102     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800821q     Document Type: Article

References (70)

1. (a) Arduengo, A. J.; Dias, H. V. R.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530-5534.
2. (b) Herrmann, W. A.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2163-2187.
3. (c) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
4. (d) Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-214.
5. (e) Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
6. (f) Sanford, M. S.; Love, J. A.; Grubbs, R. H. Organometallics 2001, 20, 5314-5318.
7. (g) Scott, N. M.; Nolan, S. P. Eur. J. Org. Chem. 2005, 1815-1828.
8. (a) Crabtree, R. H. J. Organomet. Chem. 2005, 690, 5451-5457.
9. (b) Diez-Gonzalez, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874-883.
10. (a) Corberan, R.; Peris, E. Organometallics 2008, 27, 1954-1958.
11. (b) Voutchkova, A. M.; Gnanamgari, D.; Jakobsche, C. E.; Butler, C.; Miller, S. J.; Parr, J.; Crabtree, R. H. J. Organomet. Chem. 2008, 693, 1815-1821.
12. (c) Poyatos, M.; McNamara, W.; Incarvito, C.; Peris, E.; Crabtree, R. H. Chem. Commun. 2007, 2267-2269.
13. (d) Gnanamgari, D.; Moores, A.; Rajaseelan, E.; Crabtree, R. H. Organometallics 2007, 26, 1226-1230.
14. (a) Dragutan, V.; Dragutan, I.; Delaude, L.; Demonceau, A. Coord. Chem. Rev. 2007, 251, 765-794.
15. (b) Liu, Z.; Zhang, T.; Shi, M. Organometallics 2008, 27, 2668-2671.
16. (c) Xi, Z.; Liu, B.; Chen, W. J. Org. Chem. 2008, 73, 3954-3957.
17. (a) Jimenez, M. V.; Perez-Torrente, J. J.; Bartolome, M. I.; Gierz, V.; Lahoz, F. J.; Oro, L. A. Organometallics 2008, 27, 224-234.
18. (b) Poyatos, M.; Maisse-Francois, A.; Bellemin-Laponnaz, S.; Gade, L. H. Organometallics 2006, 25, 2634-2641.
19. (a) Kuhl, O. Chem. Soc. Rev. 2007, 36, 592-607.
20. (b) Pugh, D.; Danopoulos, A. A. Coord. Chem. Rev. 2007, 251, 610-641.
21. (c) Ray, L.; Shaikh, M. M; Ghosh, P. Organometallics 2007, 26, 958-964.
22. (a) Lee, C. C.; Ke, W. C.; Chan, K. T.; Lai, C. L.; Hu, C. H.; Lee, H. M. Chem.-Eur. J. 2007, 13, 582-591.
23. (b) Hahn, F. E.; Jahnke, M. C.; Pape, T. Organometallics 2006, 25, 5927-5936.
24. (c) Yang, C. L.; Lee, H. M.; Nolan, S. P. Org. Lett. 2001, 3, 1511-1514.
25. (a) Danopoulos, A. A.; Tsoureas, N.; Macgregor, S. A.; Smith, C. Organometallics 2007, 26, 253-263.
26. (b) Mas-Marza, E.; Sanau, M.; Peris, E. J. Organomet. Chem. 2005, 690, 5576-5580.
27. (c) Mas-Marza, E.; Sanau, M.; Peris, E. Inorg. Chem. 2005, 44, 9961-9967.
28. Gade, L. H.; Bellemin-Laponnaz, S. Coord. Chem. Rev. 2007, 251, 718-725.
29. (a) Liao, C. Y.; Chan, K. T.; Zeng, J. Y.; Hu, C. H.; Tu, C. Y.; Lee, H. M. Organometallics 2007, 26, 1692-1702.
30. (b) Spencer, L. P.; Winston, S.; Fryzuk, M. D. Organometallics 2004, 23, 3372-3374.
31. (c) Arnold, P. L.; Liddle, S. T. Chem. Commun. 2006, 3959-3971.
32. Herrmann, W. A.; Goossen, L. J.; Spiegler, M. J. Organomet. Chem. 1997, 547, 357-366.
33. (a) Corberan, R.; Sanau, M.; Peris, E. Organometallics 2007, 26, 3492-3498.
34. (b) Wang, R. H.; Zeng, Z.; Twamley, B.; Piekarski, M. M.; Shreeve, J. M. Eur. J. Org. Chem. 2007, 655-661.
35. (c) Huynh, H. V.; Yeo, C. H.; Tan, G. K. Chem. Commun. 2006, 3833-3835.
36. (d) Arnold, P. L.; Blake, A. L.; Wilson, C. Chem.-Eur. J. 2005, 11, 6095-6099.
37. (e) Hahn, F. E.; Holtgrewe, C.; Pape, T.; Martin, M.; Sola, E.; Oro, L. A. Organometallics 2005, 24, 2203-2209.
38. (f) Chen, J. C. C.; Lin, I. J. B. Organometallics 2000, 19, 5113-5121.
39. Yamaguchi, K.; Koike, T.; Kotani, M.; Matsushita, M.; Shinachi, S.; Mizuno, N. Chem.-Eur. J. 2005, 11, 6574-6582.
40. Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226-236.
41. (a) Skucas, E.; Ngai, M. Y.; Komanduri, V.; Krische, M. J. Ace. Chem. Res. 2007, 40, 1394-1401.
42. (b) Hamid, M.; Slatford, P. A.; Williams, J. M. J. Adv. Synth. Catal. 2007, 349, 1555-1575.
43. (c) Guillena, G.; Ramon, D. J.; Yus, M. Angew. Chem., Int. Ed. 2007, 46, 2358-2364.
44. (d) Fujita, K.; Yamaguchi, R. Synlett., 2005, 560-571.
45. (a) Cho, C. S.; Kim, B. T.; Kim, H. S.; Kim, T. J.; Shim, S. C. Organometallics 2003, 22, 3608-3610.
46. (b) da Costa, A. P.; Viciano, M.; Sanau, M.; Merino, S.; Tejeda, J.; Peris, E.; Royo, B. Organometatlics 2008, 27, 1305-1309.
47. (c) Fujita, K.; Asai, C.; Yamaguchi, T.; Hanasaka, F.; Yamaguchi, R. Org. Lett. 2005, 7, 4017-4019.
48. (d) Martinez, R.; Ramon, D. J.; Yus, M. Tetrahedron 2006, 62, 8982-8987.
49. (e) Viciano, M.; Sanau, M.; Peris, E. Organometallics 2007, 26, 6050-6054.
50. (f) Gnanamgari, D.; Leung, C. H.; Schley, N. D.; Hilton, S. T.; Crabtree, R. H. Org. Biomol. Chem. 2008, 6, 4442-4445.
51. (a) Fujita, K.; Li, Z. Z.; Ozeki, N.; Yamaguchi, R. Tetrahedron Lett. 2003, 44, 2687-2690.
52. (b) Fujita, K. I.; Fujii, T.; Yamaguchi, R. Org. Lett. 2004, 6, 3525-3528.
53. (c) Tillack, A.; Hollmann, D.; Michalik, D.; Beller, M. Tetrahedron Lett. 2006, 47, 8881-8885.
54. (d) Hamid, M.; Williams, J. M. J. Chem. Commun. 2007, 725, 727.
55. (a) Chianese, A. R.; Li, X. W.; Janzen, M. C.; Faller, J. W.; Crabtree, R. H. Organometallics 2003, 22, 1663-1667.
56. (b) Lin, I. J. B.; Vasam, C. S. Comments Inorg. Chem. 2004, 25, 75-129.
57. (a) Tanabe, Y.; Hanasaka, F.; Fujita, K.; Yamaguchi, R. Organometallics 2007, 26, 4618-4626.
58. (b) Corberan, R.; Sanau, M.; Peris, E. J. Am. Chem. Soc. 2006, 128, 3974-3979.
59. (c) Hanasaka, F.; Fujita, K.; Yamaguchi, R. Organometallics 2005, 24, 3422-3433.
60. (d) Hanasaka, F.; Fujita, K. I.; Yamaguchi, R. Organometallics 2004, 23, 1490-1492.
61. Fujita, K.; Tanino, N.; Yamaguchi, R. Org. Lett. 2007, 9, 109-111.
62. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069-1094.
63. Fujita, K. I.; Enoki, Y.; Yamaguchi, R. Tetrahedron 2008, 64, 1943-1954.
64. Ball, R. G.; Graham, W. A. G.; Heinekey, D. M.; Hoyano, J. K.; McMaster, A. D.; Mattson, B. M.; Michel, S. T. Inorg. Chem. 1990, 29, 2023-5.
65. Hodson, E.; Simpson, S. J. Polyhedron 2004, 23, 2695-2707.
66. Occhipinti, G.; Bjorsvik, H. R.; Tornroos, K. W.; Furstner. A.; Jensen, V. R. Organometallics 2007, 26, 4383-4385.
67. Gardiner, M. G.; Herrmann, W. A.; Reisinger, C. P.; Schwarz, J.; Spiegler, M. J. Organomet. Chem. 1999, 572, 239-247.
68. CrystalClear and CrystalStructure; Rigaku/MSC: The Woodlands, TX, 2005.
69. Sheldrick, G. M. SHELXS (direct methods); 1990. Sheldrick, G. M; Schneider, T. R. SHELXL (refinement); 1997.
70. 2.