(PhTe)2-mediated intramolecular radical cyclization of o-ethynylaryl isocyanides leading to bistellurated quinolines upon visible-light irradiation

Organic Letters

Volumn 11, Issue 15, 2009, Pages 3422-3424

  Mitamura, Takenori ^a   Iwata, Kimiyo ^a   Ogawa, Akiya ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 68149122176     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901267h     Document Type: Article

References (37)

1. For the radical addition of organic disulfides, see: (a) Heiba, E. I.; Dessau, R. M. J. Org. Chem. 1967, 32, 3837.
2. (b) Takaguchi, Y.; Katayose, Y.; Yanagimoto, Y.; Motoyoshiya, J.; Aoyama, H.; Wakahara, T.; Maeda, Y.; Akasaka, T. Chem. Lett. 2003, 32, 1124.
3. For the radical addition of organic diselenides to acetylenes, see: (a) Back, T. G.; Krishna, M. V. J. Org. Chem. 1988, 53, 2533.
4. (b) Ogawa, A.; Yokoyama, H.; Yokoyama, K.; Masawaki, T.; Kambe, N.; Sonoda, N. J. Org. Chem. 1991, 56, 5721.
5. (c) Tsuchii, K.; Doi, M.; Ogawa, L; Einaga, Y.; Ogawa, A. Bull. Chem. Soc. Jpn. 2005, 78, 1534.
6. Ogawa, A.; Yokoyama, K.; Obayashi, R.; Han, L.-B.; Kambe, N.; Sonoda, N. Tetrahedron 1993, 49, 1177.
7. 2, see: (a) Ogawa, A.; Obayashi, R.; Ine, H.; Tsuboi, Y.; Sonoda, N.; Hirao, T. J. Org. Chem. 1998, 63, 881.
8. (b) Tsuchii, K.; Tsuboi, Y.; Kawaguchi, S.; Takahashi, J.; Sonoda, N.; Nomoto, A.; Ogawa, A. J. Org. Chem. 2007, 72, 415.
9. For the radical reactions by using a mixed system of (PhS)2 and (PhTe)2, see: (a) Ogawa, A.; Ogawa, I.; Obayashi, R.; Umezu, K.; Doi, M.; Hirao, T. J. Org. Chem. 1999, 64, 86.
10. (b) Mitamura, T.; Tsuboi, Y.; Iwata, K.; Tsuchii, K.; Nomoto, A.; Sonoda, M.; Ogawa, A. Tetrahedron Lett. 2007, 48, 5953.
11. Ogawa, A. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 2, p 813.
12. (a) Bachi, M. D.; Bar-Ner, N.; Melman, A. J. Org. Chem. 1996, 61, 7116.
13. (b) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213.
14. (c) Tokuyama, H.; Watanabe, M.; Hayashi, Y.; Kurokawa, T.; Peng, G.; Fukuyama, T. Synlett 2001, 1403.
15. (d) Sumi, S.; Matsumoto, K.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2003, 5, 1891.
16. (e) Kotani, M.; Yamago, S.; Satoh, A.; Tokuyama, H.; Fukuyama, T. Synlett 2005, 1893.
17. (f) Minozzi, M.; Nanni, D.; Zanardi, G.; Calestani, G. Arkivoc 2006, VI, 6.
18. Unfortunately, o-ethynylaryl isocyanides are unstable to isolate. Thus, isocyanides were employed for the radical cyclization reaction without purification prior to use.
19. 2, oligomerization took place exclusively. See: Curran, D. P.; Martin-Esker, A. A.; Ko, S. B.; Newcomb, M. J. Org. Chem. 1993, 58, 4691.
20. -1); see
21. (b) Schiesser, C. H.; Wild, L. M. Tetrahedron 1996, 52, 13265.
22. 2provided a complex mixture including 3a and 4a.
23. Another possible reaction pathway is the Bergman-like cyclization under photoirradiation to generate a biradical species and sequential abstraction of telluro groups. However, the determination of the precise reaction pathways should wait for further detailed mechanistic study.
24. (a) Barton, D. H. R.; Ramesh, M. J. Am. Chem. Soc. 1990, 112, 891.
25. (b) Ueda, Y.; Watanabe, H.; Uemura, J.; Uneyama, K. Tetrahedron Lett. 1993, 34, 7933.
26. (c) Crich, D.; Chen, C.; Hwang, J.-T.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937.
27. (d) Nishibayashi, Y.; Cho, C. S.; Uemura, S. J. Organomet. Chem. 1996, 507, 197.
28. (e) Engman, L.; Laws, M. J.; Malmström, J.; Schiesser, C. H.; Zugaro, L. M. J. Org. Chem. 1999, 64, 6764.
29. (f) Yamago, S.; Miyazoe, H.; Goto, R.; Hashidume, M.; Sawazaki, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 3697.
30. (g) Fujiwara, S.; Shimizu, Y.; Shin-ike, T.; Kambe, N. Org. Lett. 2001, 3, 2085.
31. (h) Zeni, G.; Lüdtke, D. S.; Panatieri, R. B.; Braga, A. L. Chem. Rev. 2006, 106, 1032.
32. (i) Yamago, S.; Matsumoto, A. J. Org. Chem. 2008, 73, 7300.
33. (j) Fujiwara, S.; Shimizu, Y.; Imahori, Y.; Toyofuku, M.; Shin-ike, T.; Kambe, N. Tetrahedron Lett. 2009, 50, 3628.
34. (a) Hiiro, T.; Morita, Y.; Inoue, T.; Kambe, N.; Ogawa, A.; Ryu, I.; Sonoda, N. J. Am. Chem. Soc. 1990, 112, 455.
35. (b) Ogawa, A.; Tsuboi, Y.; Obayashi, R.; Yokoyama, K.; Ryu, I.; Sonoda, N. J. Org. Chem. 1994, 59, 1600.
36. (c) Tucci, F. C.; Chieffi, A.; Comasseto, J. V.; Marino, J. P. J. Org. Chem. 1996, 67, 4975.
37. (d) Moraes, D. N.; Barrientos-Astigarraga, R. E.; Castelani, P.; Comasseto, J. V. Tetrahedron 2000, 56, 3327.