Iron(II) bromide-catalyzed synthesis of benzimidazoles from aryl azides

Organic Letters

Volumn 10, Issue 15, 2008, Pages 3367-3370

  Shen, Meihua ^a   Driver, Tom G ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; AZIDE; BENZALDEHYDE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BROMIDE; FERROUS ION; RHODIUM;

ARTICLE; CHEMISTRY; SYNTHESIS;

ANILINE COMPOUNDS; AZIDES; BENZALDEHYDES; BENZIMIDAZOLES; BROMIDES; FERROUS COMPOUNDS; RHODIUM;

EID: 49649102647     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801227f     Document Type: Article

References (67)

1. For reviews, see: (a) Lang, S.; Murphy, J. A. Chem. Soc. Rev. 2006, 35, 146.
2. (b) Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188.
3. (c) Judd, W. R.; Katz, C. E.; Aubé, J. Sci. Synth. 2005, 21, 133.
4. (d) Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297.
5. (e) L'abbé, G. Angew. Chem., Int. Ed. 1975, 14, 775.
6. For aryl azides, see: (a) Sundberg, R. J.; Gillespie, D. W.; DeGraff, B. A. J. Am. Chem. Soc. 1975, 97, 6193.
7. (b) Sundberg, R. J.; Russell, H. F.; Ligon, W. V.; Lin, L.-S. J. Org. Chem. 1972, 37, 719.
8. (c) von E. Doering, W.; Odum, R. A Tetrahedron 1966, 22, 81.
9. (d) Smith, P. A. S.; Hall, J. H. J. Am. Chem. Soc. 1962, 84, 480.
10. (e) Huisgen, R. Angew. Chem. 1955, 67, 749.
11. (f) Smith, P. A. S.; Brown, B. B. J. Am. Chem. Soc. 1951, 73, 2435.
12. For vinyl azides, see: (a) Moody, C. J. Stud. Nat. Prod. Chem. 1988, 1, 163.
13. (b) Henn, L.; Hickey, D. M. B.; Moody, C. J.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1984, 2189.
14. (c) Hemetsberger, H.; Knittel, D. Monatsh. Chem. 1972, 103, 194.
15. (d) Hemetsberger, H.; Knittel, D.; Weidmann, H. Monatsh. Chem. 1970, 101, 161.
16. (e) Isomura, K.; Kobayashi, S.; Taniguchi, H. Tetrahedron Lett. 1968, 9, 3499.
17. For reviews, see: (a) Söderberg, B. C. G. Curr. Org. Chem. 2000, 4, 727.
18. (b) Moody, C. J. Comprehensive Organic Synthesis; Trost, B. M., ; Fleming, I., ; Ley, S., Eds.; Pergamon: Oxford, 1991; Vol. 7, p 21.
19. (c) Azides and Nitrenes, Reactivity and Utility; Scriven, E. F. V., Ed.; Academic Press: London, 1984.
20. (d) Nitrenes; Lwowski, Ed.; Wiley: New York, 1970.
21. (a) Milligan, G. L.; Mossman, C. J.; Aubé, J. J. Am. Chem. Soc. 1995, 117, 10449.
22. (b) Gracias, V.; Milligan, G. L.; Aubé, J. J. Am. Chem. Soc. 1995, 117, 8047.
23. (c) Pearson, W. H.; Walavalkar, R.; Schkeryantz, J M.; Fang, W.-k.; Blickensdorf, J. D J. Am. Chem. Soc. 1993, 115, 10183.
24. (d) Aubé, J.; Milligan, G. L. J. Am. Chem. Soc. 1991, 113, 8965.
25. Thermal [3 + 2] cycloaddition reactions of azides often afford mixtures of 1,4- and 1,5-disubstituted triazoles. See: Huisgen, R. 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Pergamon: Oxford, 1984; p 1.
26. The formation of tars and dimerization products can plague thermal reactions of azides. See: Abramovitch, R. A.; Challand, S. R.; Scriven, E. F. V. J. Am. Chem. Soc. 1972, 94, 1374.
27. For nitogen-atom transfer reviews, see: (a) Cenini, S.; Gallo, E.; Caselli, A.; Ragaini, F.; Fantauzzi, S.; Piangiolino, C. Coord. Chem. Rev. 2006, 250, 1234.
28. (b) Katsuki, T. Chem. Lett. 2005, 34, 1304.
29. (a) Ruppel, J. V.; Jones, J. E.; Huff, C. A.; Kamble, R. M.; Chen, Y.; Zhang, X. P. Org. Lett. 2008, 10, 1995.
30. (b) Bosch, L.; Vilarrasa, J. Angew. Chem., Int. Ed. 2007, 41, 3926.
31. (c) Ruppel, J. V.; Kamble, R. M.; Zhang, X. P. Org. Lett. 2007, 9, 4889.
32. (d) Chiba, S.; Wang, Y. F.; Lapointe, G.; Narasaka, K. Org. Lett. 2008, 10, 313.
33. (e) Díez-González, S.; Correa, A.; Cavallo, L.; Nolan, S. P. Chem.-Eur. J. 2006, 12, 7558.
34. (f) Zhang, L.; Chen, X.; Xue, P.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G. J. Am. Chem. Soc. 2005, 127, 15998.
35. (g) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
36. (h) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
37. (i) Pearson, W. H.; Hutta, D. A.; Fang, W. -k. J. Org. Chem. 2000, 65, 8326.
38. (j) Bach, T.; Körber, C. J. Org. Chem. 2000, 65, 2358.
39. (a) Shen, M.; Leslie, B. E.; Driver, T. G. Angew. Chem., Int. Ed. 2008, 47, 5056.
40. (b) Dong, H.; Shen, M.; Redford, J. E.; Stokes, B. J.; Pumphrey, A. L.; Driver, T. G. Org. Lett. 2007, 9, 5191.
41. (c) Stokes, B. J.; Dong, H.; Leslie, B. E.; Pumphrey, A. L.; Driver, T. G. J. Am. Chem. Soc. 2007, 129, 7500.
42. For reports on the thermolysis of 2-azidoaryl imines, see: (a) Wallace, J. M.; Söderberg, B. C. G.; Hubbard, J. W. Synth. Commun. 2006, 36, 3425.
43. (b) Hall, J. H.; Famm, D. R. J. Org. Chem. 1965, 30, 2092.
44. (c) Krbechek, L.; Takimoto, H. J. Org. Chem. 1964, 29, 3630.
45. (a) Demko, Z. P.; Sharpless, K. B. Org. Lett. 2001, 3, 4091.
46. (b) Hall, J. H.; Patterson, E. J. Am. Chem. Soc. 1967, 89, 5856.
47. Please refer to the Supporting Information.
48. 3, see: (a) Takeuchi, H.; Shiobara, Y.; Kawamoto, H.; Koyama, K. J. Chem. Soc., Perkin Trans. 1 1990, 321.
49. (b) Takeuchi, H.; Maeda, M.; Mitani, M.; Koyama, K. J. Chem. Soc., Perkin Trans. 1 1987, 57.
50. (c) Takeuchi, H.; Shiobara, Y.; Mitani, M.; Koyama, K. J. Chem. Soc., Chem. Commun. 1985, 1251.
51. (d) Takeuchi, H.; Maeda, M.; Mitani, M.; Koyama, K. J. Chem. Soc., Chem. Commun. 1985, 287.
52. For iron-catalyzed transformations of azides, see: (a) ref 9j.
53. (b) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955.
54. (c) Bach, T.; Schlummer, B.; Harms, K. Chem.-Eur. J. 2001, 7, 2581.
55. (d) Bach, T.; Schlummer, B.; Harms, K. Chem. Commun. 2000, 287.
56. (e) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015.
57. 2.
58. Attempts to perform both steps in one flask without isolation of the intermediate aryl imine were not successful.
59. While iron(II) salts have been reported to catalyze nitrogen-atom transfer reactions (see refs 9j and 15), the lack of decomposition products (e.g., azo compounds, tars, anilines) suggests that a nitrenoid intermediate is not involved.
60. For related mechanistic studies of Lewis acid-mediated additions of azides to oxocarbenium ions, see: (a) Katz, C. E.; Ribelin, T.; Withrow, D.; Basseri, Y.; Manukyan, A. K.; Bermudez, A.; Nuera, C. G.; Day, V. W.; Powell, D. R.; Poutsma, J. L.; Aubé, J. J. Org. Chem. 2008, 73, 3318.
61. (b) Hewlett, N. D.; Aubé, J.; Radkiewicz-Poutsma, J. L. J. Org. Chem. 2004, 69, 3439.
62. For leading reports of iron(II)-imine crystal structures, see: (a) Bart, S. C.; Lobkovsky, E.; Bill, E.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 5302.
63. (b) Bouwkamp, M. W.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2005, 127, 9660.
64. For leading reports, which compare the Lewis acidity of transition metals, see: (a) Yamamoto, Y. J. Org. Chem. 2007, 72, 7817.
65. (b) Kobayashi, S.; Busujuma, T.; Nagayama, S. Chem.-Eur. J. 2000, 6, 3491.
66. (c) Pearson, R. G. Inorg. Chem. 1988, 27, 734.
67. Alternatively, the 1H-benzimidazole product could tautomerize. For a recent review on these processes in N-heterocycles, see: Elguero, J.; Katritzky, A. R.; Denisko, O. V. Adv. Heterocycl. Chem. 2000, 76, 1.