Efficient and practical synthesis of 4(5)-aryl-1H-imidazoles and 2,4(5)-diaryl-1H-imidazoles via highly selective palladium-catalyzed arylation reactions

Journal of Organic Chemistry

Volumn 72, Issue 22, 2007, Pages 8543-8546

  Bellina, Fabio ^a   Cauteruccio, Silvia ^a   Rossi, Renzo ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATION; ARYLBORONIC ACIDS; PHASE TRANSFER;

BORON COMPOUNDS; BYPRODUCTS; CATALYSIS; LIGANDS; PALLADIUM COMPOUNDS;

CRYSTALLINE MATERIALS;

4(5) BROMO 1H IMIDAZOLE; BROMIDE; IMIDAZOLE DERIVATIVE; IODIDE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SUZUKI REACTION; SYNTHESIS;

CATALYSIS; IMIDAZOLES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 35548986276     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701496p     Document Type: Article

References (59)

1. Ellis, G. P.; Epstein, C.; Fitzmaurice, C.; Golberg, L.; Lord, G. H. J. Pharm. Pharmacol. 1964, 16, 400.
2. Li, Y.-K.; Hsu, H.-S.; Chang, L.-F.; Chen, G. J. Biochem. 1998, 123, 416.
3. Kim, D.-K.; Jang, Y.; Lee, H. S.; Park, H.-J.; Yoo, J. J. Med. Chem. 2007, 50, 3143.
4. Elliott, R. L.; Oliver, R. M.; LaFlamme, J. A.; Gillaspy, M. L.; Hammond, M.; Hank, R. F.; Maurer, T. S.; Baker, D. L.; DaSilva-Jardine, P. A.; Stevenson, R. W.; Mack, C. M.; Cassella, J. V. Bioorg. Med. Chem. Lett. 2003, 13, 3593.
5. (a) Liberatore, A.-M.; Schultz, J.; Pommier, J.; Barthelemy, M. A.; Huchet, M.; Chabrier, P. E.; Bigg, D. Bioorg. Med. Chem. Lett. 2004, 14, 3521.
6. (b) Liberatore, A.-M.; Schultz, J.; Favre-Guilmard, C.; Pommier, J.; Lannay, J.; Pawlowski, E.; Barthelemy, M. A.; Huchet, M.; August, M.; Chabrier, P. E.; Bigg, D. Bioorg. Med. Chem. Lett. 2007, 17, 1746.
7. (a) Bolós, J. Mini-Rev. Med. Chem. 2005, 5, 857.
8. (b) DeLuca, L. Curr. Med. Chem. 2006, 13, 1.
9. (c) Diller, D. J.; Lin, T. H.; Metzger, A. Curr. Top. Med. Chem. 2005, 5, 953.
10. (d) Bellina, F.; Cauteruccio, S.; Rossi, R. Tetrahedron 2007, 63, 4571.
11. Selected references: (a) Zhong, Y.-L.; Lee, J.; Reamer, R. A.; Askin, D. Org. Lett. 2004, 6, 929.
12. (b) Kong, Y. C.; Kim, K. J. J. Heterocycl. Chem. 1999, 36, 911.
13. (c) Cavalieri, B.; Volpe, G.; Arioli, V.; Parenti, F. Arzneim.-Forsch. Drug Res. 1977, 27, 1889.
14. For a review on the synthetic methods utilized to prepare 4(5)-aryl-1H-imidazole derivatives which are p38 MAP kinase inhibitors, see: Murry, J. A. Curr. Opin. Drug Discovery Dev. 2003, 6, 945.
15. ten Have, R.; Huisman, M.; Meetsma, A.; van Leusen, A. M. Tetrahedron 1997, 53, 11355.
16. Jetter, M. C.; Reitz, A. B. Synthesis 1998, 829.
17. Heerding, D. A.; Chan, G.; De Wolf, W. E., Jr.; Fosberry, A. P.; Janson, C. A.; Jaworski, D. D.; McManus, E.; Miller, W. H.; Moore, T. D.; Payne, D. J.; Qiu, X.; Rittenhouse, S. F.; Slater-Radosti, C.; Smith, W.; Takata, D. T.; Vaidya, K. S.; Yuan, C. C. K.; Huffman, W. F. Bioorg. Med. Chem. Lett. 2001, 11, 2061.
18. (a) Iddom, B.; Lim, B. L. J. Chem. Soc., Perkin Trans. 1 1983, 735.
19. (b) Stensiö, K. E.; Wahlberg, K.; Wahren, R. Acta Chem. Scand., Sect. B 1973, 27, 2179.
20. Li, B.; Chiu, C. K.-F.; Hank, R. F.; Murry, J.; Roth, J.; Tobiassen, H. Org. Process Res. Dev. 2002, 6, 682.
21. Voets, M.; Antes, I.; Scherer, C.; Müller-Vieira, U.; Biemel, K.; Barassin, C.; Marchais-Oberwinkler, S.; Hartmann, R. W. J. Med. Chem. 2005, 48, 6632.
22. Langhammer, I.; Erker, T. Heterocycles 2005, 65, 1975.
23. Zuliani, V.; Cocconcelli, G.; Fantini, M.; Chiron, C.; Rivara, M. J. Org. Chem. 2007, 72, 4551.
24. (a) Bellina, F.; Calandri, C.; Cauteruccio, S.; Rossi, R. Tetrahedron 2007, 63, 1970.
25. (b) Bellina, F.; Calandri, C.; Cauteruccio, S.; Rossi, R. Eur. J. Org. Chem. 2007, 2147.
26. (c) Bellina, F.; Cauteruccio, S. Rossi, R. Eur. J. Org. Chem. 2006, 1379.
27. (d) Bellina, F.; Cauteruccio, S.; Mannina, L.; Rossi, R.; Viel, S. Eur. J. Org. Chem. 2006, 693.
28. (e) Bellina, F.; Rossi, R. Tetrahedron 2006, 62, 7213.
29. (f) Bellina, F.; Cauteruccio, S.; Mannina, L.; Rossi, R.; Viel, S. J. Org. Chem. 2005, 70, 3997.
30. For recent reviews on the Suzuki-Miyaura reactions, see: (a) Bellina, F.; Carpita, A.; Rossi, R. Synthesis 2004, 2419.
31. (b) Miyaura, N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., de Meijere, A., Eds.; Wiley-VCH: New York, 2004; Chapter 2.
32. (c) Miyaura, N Top. Curr. Chem. 2002, 219, 11.
33. For examples of Pd-catalyzed Suzuki-Miyaura reactions performed under phase-transfer conditions, see: (a) Bellina, F.; Anselmi, C.; Martina, F.; Rossi, R. Eur. J. Org. Chem. 2003, 2290.
34. (b) Zhang, J.; Blazecka, P. G.; Belmont, D.; Davidson, J. G. Org. Lett. 2002, 4, 4559.
35. For selected examples of Pd-catalyzed C-arylations of free (NH)-azoles with aryl halides, see: (a) Akita, Y.; Itagaki, Y.; Takizawa, S.; Ohta, A. Chem. Pharm. Bull. 1989, 37, 1477 (indole).
36. (b) Rieth, R. D.; Mankad, N. P.; Calimano, E.; Sadighi, J. P. Org. Lett. 2004, 6, 3981 (pyrrole).
37. (c) Ref 17a (imidazole, benzimidazole, indole).
38. (d) Ref 17c (imidazole, benzimidazole, indole).
39. (d) Wang, X.; Gribkov, D. V.; Sames, D. J. Org. Chem. 2007, 72, 1476 (indole derivatives, pyrrole).
40. (a) Morita, D. K.; Stille, J. K.; Norton, J. R. J. Am. Chem. Soc. 1995, 117, 8576.
41. (b) O'Keefe, D. F.; Dannock, M. C.; Marcuccio, S. M. Tetrahedron Lett. 1992, 33, 6679.
42. (c) Kong, K.-C.; Cheng, C.-H. J. Am. Chem. Soc. 1991, 113, 6313.
43. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
44. For selected examples, see: (a) Pvisa-Art, S.; Satoh, T.; Kawamura, M.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467.
45. (b) Li, W.; Nelson, D. P.; Jensen, M. S.; Hoerrner, R. S.; Javadi, G. J.; Cai, D.; Larsen, D. D. Org. Lett. 2003, 5, 4835.
46. (c) Park, C. H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
47. (d) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050.
48. (e) Zhuralev, F. A. Tetrahedron Lett. 2006, 47, 2929.
49. (f) Touré, B. B.; Lane, B. S.; Sames, D. Org. Lett. 2006, 8, 1979.
50. (g) Chuprakov, S.; Chedrnyak, N.; Dudnik, A. S.; Gevorgyan, V. Org. Lett. 2007, 9, 2333.
51. For reviews on the transition-metal-catalyzed direct arylation of heteroarenes, see: (a) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211.
52. (b) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
53. (c) Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichimica Acta 2007, 40, 35.
54. (d) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 1173.
55. (e) Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200.
56. Garcia-Cuadrado, D.; de Mendoza, P.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2007, 129, 6880.
57. Amatore, C.; Jutand, A. J. Organomet. Chem. 1999, 576, 254.
58. For a discussion, see: (a) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047.
59. (b) Grushin, V. V.; Alper, H. Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, 1999; pp 193-226.