Copper- and palladium-catalyzed intramolecular aryl guanidinylation: An efficient method for the synthesis of 2-aminobenzimidazoles

Organic Letters

Volumn 5, Issue 2, 2003, Pages 133-136

  Evindar, Ghotas ^a   Batey, Robert A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; COPPER; GUANIDINE; HALIDE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; 2 AMINOBENZIMIDAZOLE; 2-AMINOBENZIMIDAZOLE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS; CHEMISTRY;

BENZIMIDAZOLES; CATALYSIS; COPPER; CYCLIZATION; GUANIDINE; PALLADIUM;

EID: 0038003832     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027061h     Document Type: Article

References (40)

1. Reviews: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
2. Reviews: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
3. Reviews: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
4. (a) Shakespeare, W. C. Tetrahedron Lett. 1999, 40, 2035-2038.
5. (b) Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101-1104.
6. (c) Artamkina, G. A.; Sergeev, A. G.; Beletskaya, I. P. Tetrahedron Lett. 2001, 42, 4381-4384.
7. (d) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541.
8. (a) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362-2363.
9. (b) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913-2916.
10. Ellingboe, J. W.; Spinelli, W.; Winkley, M. W.; Nguyen, T. T.; Parsons, R. W.; Moubarak, I. F.; Kitzen, J. M.; Von Engen, D.; Bagli, J. F. J. Med. Chem. 1992, 35, 705-716.
11. (a) Janssens, F.; Torremans, J.; Janssen, M.; Stokbroekx, R. A.; Luyckx, M.; Janssen, P. A. J. J. Med. Chem. 1985, 28, 1934-1943.
12. (b) Janssens, F.; Torremans, J.; Janssen, M.; Stokbroekx, R. A.; Luyckx, M.; Janssen, P. A. J. J. Med. Chem. 1985, 28, 1925-1933.
13. (c) Janssens, F.; Torremans, J.; Janssen, M.; Stokbroekx, R. A.; Luyckx, M.; Janssen, P. A. J. J. Med. Chem. 1985, 28, 1943-1947.
14. Hong, Y.; Tanoury, G. J.; Wilkinson, S. H.; Bakale, R. P.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 1997, 38, 5607-5610.
15. Barrett, I. C.; Kerr, M. A. Tetrahedron Lett. 1999, 40, 2439-2442.
16. Bendale, P. M.; Sun, C.-M. J. Comb. Chem. 2002, 4, 359-361.
17. (a) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609-3612.
18. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
19. (c) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218.
20. (d) Zhao, S.; Miller, A. K.; Berger, J.; Flippin, L. A. Tetrahedron Lett. 1996, 37, 4463-4466.
21. (e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133-1135.
22. (f) Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525-7546.
23. (g) Song, J. J.; Yee, N. K. Org. Lett. 2000, 2, 519-521.
24. (a) Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 1028-1030.
25. (b) Aoki, K.; Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 3068-3073.
26. (c) Abouabdellah, A.; Dodd, R. H. Tetrahedron Lett. 1998, 39, 2119-2122.
27. (d) Emoto, T.; Kubosaki, N.; Yamagiwa, Y.; Kamikawa, T. Tetrahedron Lett. 2000, 41, 355-358.
28. (e) Brown, J. K. Tetrahedron Lett. 2000, 41, 1623-1626.
29. (f) Song, J. J.; Yee, N. K. Org. Lett. 2000, 2, 519-521.
30. (g) Song, J. J.; Yee, N. K. Tetrahedron Lett. 2001, 42, 2937-2940.
31. (h) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402-3415.
32. (i) Gaertzen, O.; Buchwald, S. L. J. Org. Chem. 2002, 67, 465-475.
33. Brain, C. T.; Brunton, S. A. Tetrahedron Lett. 2002, 43, 1893-1895.
34. (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729.
35. (b) Wolter, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803-3805.
36. (c) Hennessy, E. J.; Buchwald, S. L. Org. Lett. 2002, 4, 269-272.
37. (d) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581-584.
38. (e) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
39. For an earlier review of copper-assisted nucleophilic substitutions of aryl halides, see: Lindley, J. Tetrahedron 1984, 40, 1433-1456.
40. 4 (23.1 mg, 0.1 equiv) catalyzed reactions, dried dimethoxyethane (from 4 Å molecular sieves) was used as a solvent.