Palladium-catalyzed perarylation of 3-thiophene- and 3-furancarboxylic acids accompanied by C-H bond cleavage and decarboxylation

Organic Letters

Volumn 10, Issue 9, 2008, Pages 1851-1854

  Nakano, Masaya ^a   Tsurugi, Hayato ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 55049131762     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800466b     Document Type: Article

References (57)

1. Reviews: (a) Roncali, J. Chem. Rev. 1997, 97, 173.
2. (b) Mitschke, U.; Bäuerle, P. J. Mater. Chem. 2000, 10, 1471.
3. (c) Katz, H. E.; Bao, Z.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359.
4. (d) Sun, Y.; Liu, Y.; Zhu, D. J. Mater. Chem. 2005, 15. 53.
5. (e) Perepichaka, I. F.; Perepichaka, D. F.; Meng, H.; Wudl, F. Adv. Mater. 2005, 17, 2281.
6. (f) Takimiya, K.; Kunugi, Y.; Otsubo, T. Chem. Lett. 2007, 36, 578.
7. (a) de Meijere, A., Diederich, F., Eds. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004.
8. (b) Tsuji, J. Palladium Reagents and Catalysts, 2nd ed.; John Wiley & Sons: Chichester, UK, 2004.
9. Reviews: (a) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211.
10. (b) Hassan, J.; Sévignon, M.; Gozzi, C.: Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
11. (c) Miura, M.; Satoh, T. Top. Organomet. Chem. 2005, 14, 55.
12. (d) Satoh, T.; Miura, M. Chem. Lett. 2007. 36, 200.
13. (e) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
14. (f) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
15. Reviews: (a) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97. 2879.
16. (b) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47.
17. (c) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
18. (d) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
19. (e) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
20. (f) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
21. (g) Miura, M.; Satoh, T. In Handbook ofC-H transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, Germany, 2005; 1p 223.
22. (h) Campeau, L.-C.; Fagnou, K. Chem. Commun. 2006, 1253.
23. (i) Godula, K.; Sames, D. Science 2006, 312, 67.
24. (j) Chatani, N., Ed. Directed Metallation (Top. Organomet. Chem. Vol. 24); Springer: Berlin, Germany, 2008.
25. (k) Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222.
26. Reviews: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245.
27. (b) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870.
28. (c) Murakami, M.; Ito, Y. Top. Organomet. Chem. 1999, 3, 97.
29. (d) Mitsudo, T.; Kondo, T. Synlett 2001, 309.
30. (e) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Simhai, N.; Iverson, C. N.; M̈ller, C.; Satoh, T.; Jones, W. D. J. Mol. Catal. A 2002, 189, 157.
31. (f) Catellani, M. Synlett 2003, 298.
32. (g) Nishimura, T.; Uemura, S. Synlett 2004, 201.
33. (h) Satoh, T.; Miura, M. Top. Organomet. Chem. 2005, 14, 1.
34. (a) Terao, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2001,123, 10407.
35. (b) Terao, Y.; Wakui, H.; Nomoto, M.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem. 2003, 68, 5236.
36. (c) Terao, Y.; Nomoto, M.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem. 2004, 69, 6942.
37. (d) Yokooji, A.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2004, 60, 6757.
38. (e) Nakano. M.; Satoh, T.; Miura, M. J. Org. Chem, 2006, 71, 8309.
39. (f) See also: Bíro, A. B.; Kotschy, A. Eur. J. Org. Chem. 2007, 1364.
40. (a) Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 5286.
41. (b) Yokooji, A.; Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2003,59, 5685.
42. (c) Kametani, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2000, 41, 2655.
43. Ipso-arylation: (a) Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662.
44. (b) Goossen, L. J.; Rodoriguez. N.; Melzer, B.; Linder, C; Deng, G.; Levy, L. M. J. Am. Chem. Soc. 2007, 129, 4824.
45. (c) Reference 7a. (d) Forgione, P.; Brochu, M.-C.; St-Onge, M.; Thesen, K. H.; Bailey, M. D.; Bilodeau, F. J. Am. Chem, Soc. 2006, 128, 11350. Ortho-arylation:
46. (e) Chiong, H. A.; Pham, Q.-N.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 9879.
47. (f) Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem, Soc. 2007. 129, 3510.
48. Decarboxylative ipso-vinylation: (a) Tanaka, D.; Romeril. S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 727, 10323. Decarboxylative ortho-vinylation:
49. (b) Maehara, A.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1159.
50. Synthesis of tetraarylthiophenes by cross-coupling reactions:
51. (a) Naudin. E.: Mehdi, N. E.; Soucv, C.; Breau, L.; Bélanger, D. Chem. Mater. 2001, 13, 634.
52. (b) Sun, X.; Liu, Y.; Chen, S.; Qiu, W.; Yu, G.; Ma, Y.; Qi, T. Adv. Funct. Mater. 2006, 16, 917.
53. (c) Xing, Y.; Xu, X.; Wang, F.; Lu, P. Opt. Mater. 2006, 29, 407.
54. (d) Dang, T. T.; Rasool, N.; Dang, T. T.; Reinke, H.; Langer, P. Tetrahedron Lett. 2007, 48, 845.
55. (e) Dang, Y.; Chen, Y. J. Org. Chem. 2007, 72, 6901.
56. Related perarylation of cyclopentadienes: (a) Dyker, G.; Heiermann, J.; Miura, M.; Inoh, J.; Pivsa-Art, S.: Satoh, T.; Nomura, M. Chem. Eur. J. 2000, 6, 3426.
57. (b) Kataoka, N.; Shellbv, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553.