Synthesis and redox behavior of 1,3-bis(methylthio-) and 1,3-bis(phenylthio)azulenes bearing 2- and 3-thienyl substituents by palladium-catalyzed cross-coupling reaction of 2- and 6-haloazulenes with thienylmagnesium ate complexes

European Journal of Organic Chemistry

Volumn , Issue 25, 2009, Pages 4307-4315

  Shoji, Taku ^a   Ito, Shunji ^b   Toyota, Kozo ^a   Iwamoto, Takeaki ^a   Yasunami, Masafumi ^c   Morita, Noboru ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b HIROSAKI UNIVERSITY   (Japan)

^c NIHON UNIVERSITY   (Japan)

Author keywords

Arenes; Cross coupling; Cyclic voltammetry; Electrophilic substitution

Indexed keywords

EID: 68949083025     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900508     Document Type: Article

References (43)

1. a) J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1469;
2. b) J.-P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651-2710;
3. c) L. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133-173.
4. a) D. Milstein, J. K. Stille, J. Am. Chem. Soc. 1978, 100, 3636-3638;
5. b) P. Espinet, A. M. Echavarren, Angew. Chem. Int. Ed. 2004, 43, 4704-4734.
6. a) N. Miyaura, A. Suzuki, J. Chem. Soc., Chem. Commun. 1979, 866-867;
7. b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
8. a) A. O. King, N. Okukado, E. Negishi, J. Chem. Soc., Chem. Commun. 1977, 683-684;
9. b) E. Negishi, A. O. King, N. Okukado, J. Org. Chem. 1977, 42, 1821-1823;
10. c) E. Negishi, Acc. Chem. Res. 1982, 15, 340-348;
11. d) E. Erdik, Tetrahedron 1992, 48, 9577-9648.
12. a) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1470;
13. b) S. V. Ley, A. W. Thomas, Angew. Chem. Int. Ed. 2003, 42, 5400-5449.
14. K.-P. Zeller, "Azulene" in Methoden der Organischen Chemie (Houben - Weyl) (Ed.: H. Kropf), 4th ed., Thieme, Stuttgart, Germany, 1985, vol. V, part 2c, pp. 127-418.
15. a) T. Shoji, R. Yokoyama, S. Ito, M. Watanabe, K. Toyota, M. Yasunami, N. Morita, Tetrahedron Lett. 2007, 48, 1099-1103;
16. b) T. Shoji, S. Ito, M. Watanabe, K. Toyota, M. Yasunami, N. Morita, Tetrahedron Lett. 2007, 48, 3009-3012;
17. c) J. Higashi, T. Shoji, S. Ito, K. Toyota, M. Yasunami, N. Morita, Eur. J. Org. Chem. 2008, 5823-5831;
18. d) T. Shoji, S. Ito, T. Okujima, J. Higashi, R. Yokoyama, K. Toyota, M. Yasunami, N. Morita, Eur. J. Org. Chem. 2009, 1554-1563.
19. a) S. Ito, H. Inabe, T. Okujima, N. Morita, M. Watanabe, N. Harada, K. Imafuku, J. Org. Chem. 2001, 66, 7090-7101;
20. b) S. Ito, A. Nomura, N. Morita, C. Kabuto, H. Kobayashi, S. Maejima, K. Fujimori, M. Yasunami, J. Org. Chem. 2002, 67, 7295-7302;
21. c) S. Ito, T. Okujima, N. Morita, Tetrahedron Lett. 2002, 43, 1261-1264;
22. d) S. Ito, T. Okujima, N. Morita, J. Chem. Soc. Perkin Trans. 1 2002, 1896-1905;
23. e) S. Ito, H. Inabe, N. Morita, K. Ohta, T. Kitamura, K. Imafuku, J. Am. Chem. Soc. 2003, 125, 1669-1680;
24. f) S. Ito, T. Terazono, T. Kubo, T. Okujima, N. Morita, T. Murafuji, Y. Sugihara, K. Fujimori, J. Kawakami, A. Tajiri, Tetrahedron 2004, 60, 5357-5366.
25. S. Ito, T. Kubo, N. Morita, Y. Matsui, T. Watanabe, A. Ohta, K. Fujimori, T. Murafuji, Y. Sugihara, A. Tajiri, Tetrahedron Lett. 2004, 45, 2891-2894.
26. a) S. Dumouchel, F. Mongin, F. Trécourt, G. Quéguiner, Tetrahedron Lett. 2003, 44, 2033-2035;
27. b) S. Dumouchel, F. Mongin, F. Trécourt, G. Quéguiner, Tetrahedron Lett. 2003, 44, 3877-3880;
28. c) S. Dumouchel, F. Mongin, F. Trécourt, G. Quéguiner, Tetrahedron 2003, 59, 8629-8640.
29. Part of this work was recently published in preliminary form: T. Shoji, S. Kikuchi, S. Ito, N. Morita, Heterocycles 2005, 66, 91-94.
30. Transition-metal-catalyzed coupling of 1,3-thienylazulene derivatives was recently reported: a) F. Wang, M.-Y. Han, K.-Y. Mya, Y. Wang, Y.-H. Lai, J. Am. Chem. Soc. 2005, 127, 10350-10355;
31. b) M. Oda, N. C. Thanh, M. Ikai, H. Fujikawa, K. Nakajima, S. Kuroda, Tetrahedron 2007, 63, 10608-10614.
32. M. Gingras, J. Raimundo, Y. M. Chabre, Angew. Chem. Int. Ed. 2006, 45, 1686-1712.
33. T. Kondo, T. Mitsudo, Chem. Rev. 2000, 100, 3205-3220.
34. a) A. G. Anderson Jr, R. N. McDonald, J. Am. Chem. Soc. 1959, 81, 5669-5674;
35. b) L. L. Replogle, R. M. Arluck, J. R. Maynard, J. Org. Chem. 1965, 30, 2715-2718;
36. c) L. L. Replogle, Synthesis and Redox Behavior of 1,3-Bis(methylthio- and phenylthio)azulenes J. R. Maynard, J. Org. Chem. 1967, 32, 1909-1915;
37. d) L. L. Replogle, G. C. Peters, J. R. Maynard, J. Org. Chem. 1969, 34, 2022-2024.
38. T. Asao, S. Ito, N. Morita, Tetrahedron Lett. 1989, 30, 6345-6348.
39. a) T. Shoji, S. Ito, K. Toyota, M. Yasunami, N. Morita, Tetrahedron Lett. 2007, 48, 4999-5002;
40. b) T. Shoji, H. Higashi, S. Ito, K. Toyota, M. Yasunami, N. Morita, Eur. J. Org. Chem. 2008, 1242-1252.
41. a) A. Inoue, K. Kitagawa, H. Shinokubo, K. Oshima, J. Org. Chem. 2001, 66, 4333-4339;
42. b) T. Iida, T. Wada, K. Tomimoto, T. Mase, Tetrahedron Lett. 2001, 42, 4841-4844.
43. T. Kurihara, T. Suzuki, H. Wakabayashi, S. Ishikawa, K. Shindo, Y. Shimada, H. Chiba, T. Miyashi, M. Yasunami, T. Nozoe, Bull. Chem. Soc. Jpn. 1996, 69, 2003-2008.