Catalytic annulation of heterocycles via a novel redox process involving the imidazolium salt N-heterocyclic carbene couple

Organometallics

Volumn 27, Issue 13, 2008, Pages 3153-3160

  Normand, Adrien T ^a   Yen, Swee Kuan ^b   Huynh, Han Vinh ^b   Hor, T S Andy ^b   Cavell, Kingsley J ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSIS; IONIZATION OF LIQUIDS; NICKEL; NICKEL ALLOYS; NITROGEN COMPOUNDS; SALTS;

ALKENYL; ALKYL GROUPS; CARBENE; CATALYTIC REACTIONS; DOUBLE BONDS; HETERO-CYCLES; HIGH YIELD; IMIDAZOLIUM; IMIDAZOLIUM BROMIDE; IMIDAZOLIUM SALTS; IN-SITU; MODERATE TEMPERATURES; N-HETEROCYCLIC CARBENE (NHC); OXIDATIVE ADDITION (OA); POTENTIAL BUILDING BLOCKS; PYRROLE (PY); REDOX PROCESSING; REDUCTIVE ELIMINATION (RE);

IONIC LIQUIDS;

EID: 47949114467     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800140n     Document Type: Article

References (83)

1. Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
2. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 47, 1290-1309.
3. Hahn, F. E. Angew. Chem., Int. Ed. 2006, 45, 1348-1352.
4. Arduengo, A. J., III; Gamper, S. F.; Calabrese, J. C.; Davidson, F. J. Am. Chem. Soc. 1994, 116, 4391-4394.
5. Green, J. C.; Scurr, R. G.; Arnold, P. L.; Cloke, G. N. Chem. Commun. 1997, 1963-1964.
6. Niehues, M.; Erker, G.; Kehr, G.; Schwab, P.; Fröhlich, R. Organometallics 2002, 21, 2905-2911.
7. Hu, X.; Castro-Rodriguez, I.; Olsen, K.; Meyer, K. Organometallics 2004, 23, 755-764.
8. Nemcsok, D.; Wichmann, K.; Frenking, G. Organometallics 2004, 23, 3640-3646.
9. Scott, N. M.; Dorta, R.; Stevens, E. D.; Correa, A.; Cavallo, L.; Nolan, S. P. J. Am. Chem. Soc. 2005, 127, 3516-3526.
10. Jacobsen, H.; Correa, A.; Costabile, C.; Cavallo, L. J. Organomet. Chem. 2006, 691, 4350-4358.
11. Herrmann, W. A.; Elison, M.; Fischer, J.; Kocher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. 1995, 34, 2371-2375.
12. McGuinness, D. S.; Cavell, K. J. Organometallics 2000, 19, 741-748.
13. Caddick, S.; Cloke, F. G. N.; Clentsmith, G. K. B.; Hitchcock, P. B.; McKerrecher, D.; Titcomb, L. R.; Williams, M. R. V. J. Organomet. Chem. 2001, 617-618, 635-639.
14. Böhm, V. P. W.; Weskamp, T.; Gstöttmayr, C. W. K.; Herrmann, W. A. Angew. Chem., Int. Ed. 2000, 39, 1602-1604.
15. Loch, J. A.; Albrecht, M.; Peris, E.; Mata, J.; Faller, J. W.; Crabtree, R. H. Organometallics 2002, 21, 700-706.
16. Viciu, M. S.; Germaneau, R. F.; Navarro-Fernandez, O.; Stevens, E. D.; Nolan, S. P. Organometallics 2002, 21, 5470-5472.
17. Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101-4111.
18. Navarro, O.; Marion, N.; Mei, J.; Nolan, S. P. Chem. Eur. J. 2006, 12, 5142-5148.
19. O'Brien, C. J.; Kantchev, E. A. B.; Valente, C.; Hadei, N.; Chass, G. A.; Lough, A.; Hopkinson, A. C.; Organ, M. G. Chem. Eur. J. 2006, 12, 4743-4748.
20. Organ, M. G.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Valente, C. Chem. Eur. J. 2006, 12, 4749-4755.
21. Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem., Int. Ed. 2007, 46, 2768-2813.
22. Gardiner, M. G.; Herrmann, W. A.; Reisinger, C.-P.; Schwarz, J.; Spiegier, M. J. Organomet. Chem. 1999, 572, 239-247.
23. Hill, J. E.; Nile, T. A. J. Organomet. Chem. 1977, 137, 293-300.
24. Lappert, M. F.; Maskell, R. K. J. Organomet. Chem. 1984, 264, 217-228.
25. Herrmann, W. A.; Goossen, L. J.; Köcher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. 1996, 35, 2805-2807.
26. Enders, D.; Gielen, H.; Breuer, K. Tetrahedron: Asymmetry 1997, 8, 3571-3574.
27. Herrmann, W. A.; Goossen, L. J.; Spiegier, M. Organometallics 1998, 17, 2162-2168.
28. Enders, D.; Gielen, H.; Runsink, J.; Breuer, K.; Brode, S.; Boehn, K. Eur. J. Inorg. Chem. 1998, 913-919.
29. Chen, A. C.; Ren, L.; Decken, A.; Crudden, C. M. Organometallics 2000, 19, 3459-3461.
30. Jiménez, M. V.; Pérez-Torrente, J. J.; Bartolomé, M. I.; Gierz, V.; Lahoz, F. J.; Oro, L. A. Organometallics 2008, 27, 224-234.
31. Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 1998, 37, 2490-2493.
32. Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
33. Weskamp, T.; Kohi, F. J.; Hieringer, W.; Gleich, D.; Herrmann, W. A. Angew. Chem., Int. Ed. 1999, 38, 2416-2419.
34. Kucukbay, H.; Cetinkaya, B.; Guesmi, S.; Dixneuf, P. H. Organometallics 1996, 15, 2434-2439.
35. Normand, A. T.; Cavell, K. J. Eur. J. Inorg. Chem., in press.
36. Herrmann, W. A.; Goossen, L. J.; Spiegler, M. J. Organomet. Chem. 1997, 547, 357-366.
37. Peris, E.; Mata, J.; Loch, J. A.; Crabtree, R. H. Chem. Commun. 2001, 201-202.
38. Yang, C.; Lee, H. M.; Nolan, S. P. Org. Lett. 2001, 3, 1511-1514.
39. Tsoureas, N.; Danopoulos, A. A.; Tulloch, A. A. D.; Light, M. E. Organometallics 2003, 22, 4750-4758.
40. McGuinness, D. S.; Green, M. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1998, 565, 165-178.
41. McGuinness, D. S.; Cavell, K. J.; Skelton, B. W.; White, A. H. Organometallics 1999, 18, 1596-1605.
42. McGuinness, D. S.; Cavell, K. J. Organometallics 2000, 19, 4918-4920.
43. Magill, A. M.; McGuinness, D. S.; Cavell, K. J.; Britovsek, G. J. P.; Gibson, V. C.; White, A. J. P.; Williams, D. J.; White, A. H.; Skelton, B. W. J. Organomet. Chem. 2001, 617-618, 546-560.
44. McGuinness, D. S.; Saendig, N.; Yates, B. F.; Cavell, K. J. J. Am. Chem. Soc. 2001, 123, 4029-4040.
45. McGuinness, D. S.; Cavell, K. J.; Yates, B. F. Chem. Commun. 2001, 355-356.
46. McGuinness, D. S.; Cavell, K. J.; Yates, B. F.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 2001, 123, 8317-8328.
47. Duin, M. A.; Clement, N. D.; Cavell, K. J.; Elsevier, C. J. Chem. Commun. 2003, 400-401.
48. Clement, N. D.; Cavell, K. J.; Jones, C.; Elsevier, C. J. Angew. Chem., Int. Ed. 2004, 43, 1277-1279.
49. Bacciu, D.; Cavell, K. J.; Fallis, I. A.; Ooi, L.-l. Angew. Chem., Int. Ed. 2005, 44, 5282-5284.
50. Clement, N. D.; Cavell, K. J. Angew. Chem., Int. Ed. 2004, 43, 3845-3847.
51. Normand, A. T.; Hawkes, K. J.; Clement, N. D.; Cavell, K. J.; Yates, B. F. Organometallics 2007, 26, 5352-5363.
52. Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964-13965.
53. Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 3202-3203.
54. Tan, K. L.; Vasudevan, A.; Bergman, R. G.; Ellman, J. A.; Souers, A. J. Org. Lett. 2003, 5, 2131-2134.
55. Lewis, J. C.; Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 35-38.
56. Tan, K. L.; Ellman, J. A.; Bergman, R. G. J. Org. Chem. 2004, 69, 7329-7335.
57. Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 1685-1687.
58. Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2005, 70, 6775-6781.
59. Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2006, 128, 5604-5605.
60. Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2006, 45, 1589-1591.
61. Wiedemann, S. H.; Ellman, J. A.; Bergman, R. G. J. Org. Chem. 2006, 71, 1969-1976.
62. Wiedemann, S. H.; Lewis, J. C.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2006, 128, 2452-2462.
63. Wilson, R. M.; Thalji, R. K.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2006, 8, 1745-1747.
64. Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 5332-5333.
65. Roth, T.; Morningstar, M. L.; Boyer, P. L.; Hughes, S. H.; Buckheit, R. W.; Michejda, C. J. J. Med. Chem. 1997, 40, 4199-4207.
66. Wienen, W.; Hauel, N.; Van Meel, J. C. A.; Narr, B.; Ries, U.; Entzeroth, M. Br. J. Pharmacol. 1993, 110, 245-248.
67. Kan, H.-C.; Tseng, M.-C.; Chu, Y.-H. Tetrahedron 2007, 63, 1644-1653.
68. Ni, B.; Garre, S.; Headley, A. D. Tetrahedron Lett. 2007, 48, 1999-2002.
69. Some salts are extremely hygroscopic, which precluded satisfactory elemental analysis.
70. Arrows indicate carbon atoms at which hydride insertion occurred.
71. Graham, D. C.; Cavell, K. J.; Yates, B. F. Dalton Trans. 2007, 4650-4658.
72. 46,51 provide a sound basis for the mechanism depicted in Scheme 3. Indeed, dissociation of IMes or reductive elimination of IMesHBr is unlikely to be a favorable process, considering (a) the strong Ni-NHC BDE and (b) the very exothermic C-H oxidative addition reaction of Ni(0) to imidazolium salts. We agree that a chelating NHC-olefin ligand would form very stable species; however, we think it would not be kinetically possible.
73. The last step of the catalytic cycle in the intermolecular version of this reaction is thought to proceed from a 14-electron Ni(II) species (see ref 46 for a detailed discussion), which facilitates reductive elimination. The coordination of an extra olefin might inhibit this step, by creating a stabilized 16-electron Ni(II) complex. Indeed, we observed a green coloration appearing in the course of the reaction at low loadings, indicating a Ni(II) species.
74. Schunn, R. A. Inorg. Synth. 1974, 15, 5-9.
75. Hahn, F. E.; Heidrich, B.; Pape, T.; Hepp, A.; Martin, M.; Sola, E.; Oro, L. A. Inorg. Chim. Acta 2006, 359, 4840-4846.
76. Ohno, H.; Mizumo, T.; Yoshida, M.; Suga, T. WO 2005080347, 2005.
77. Arduengo, A. J. I.; Gentry, F. P. J.; Taverkere, P. K.; Simmons, H. E. I. U.S. Patent 6,177,575, 2001.
78. Schilling, C. L.; Mulvaney, J. E. Macromolecules 1968, 1, 452-455.
79. Chen, Y. T.; Jordan, F. J. Org. Chem. 1991, 56, 5029-5038.
80. Corberan, R.; Sanau, M.; Peris, E. Organometallics 2007, 26, 3492-3498.
81. Anthony, J.; Arduengo, I.; Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich, J. R.; Marshall, W. J.; Unverzagt, M. Tetrahedron 1999, 55, 14523-14534.
82. Danopoulos, A. A.; Winston, S.; Gelbrich, T.; Hursthouse, M. B.; Tooze, R. P. Chem. Commun. 2002, 482-483.
83. Corberan, R.; Sanau, M.; Peris, E. Organometallics 2007, 26, 3492-3498.