Mercuric Triflate-(TMU)3-Catalyzed Cyclization of ω-Arylalkyne Leading to Dihydronaphthalenes

Organic Letters

Volumn 5, Issue 24, 2003, Pages 4563-4565

  Nishizawa, Mugio ^a   Takao, Hiroko ^a   Yadav, Veejendra K ^a   Imagawa, Hiroshi ^a,b   Sugihara, Takumichi ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^b INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALKYNE DERIVATIVE; MERCURIC TRIFLATE; MERCURY DERIVATIVE; NAPHTHALENE DERIVATIVE; TETRAMETHYLUREA; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CYCLIZATION; ENVIRONMENTAL TEMPERATURE;

EID: 0347254810     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035622e     Document Type: Article

References (33)

1. For reviews on metal-catalyzed carbocyclization, see: (a) Ojima, I.; Tzamarioudaki, M. L. Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (b) Negishi, E.; Coperet, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365-393. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412.
2. For reviews on metal-catalyzed carbocyclization, see: (a) Ojima, I.; Tzamarioudaki, M. L. Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (b) Negishi, E.; Coperet, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365-393. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412.
3. For reviews on metal-catalyzed carbocyclization, see: (a) Ojima, I.; Tzamarioudaki, M. L. Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (b) Negishi, E.; Coperet, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365-393. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412.
4. Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918.
5. Inoue, H.; Chatani, N.; Murai, S. J. Org. Chem. 2002, 67, 1414-1417.
6. Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055-1058.
7. (a) Larock, R. C.; Doty, M. J.; Tian, Q.; Zenner, J. M. J. Org. Chem. 1997, 62, 7536-7537.
8. (b) Fürstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264-6267.
9. Asao, N.; Shimada, T.; Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 10899-10902.
10. (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1996, 118, 6305-6306.
11. (b) Jia, C.; Piao, D.; Kitamura, T.; Fujiwara, Y. J. Org. Chem. 2000, 65, 7516-7522.
12. Koch-Pomeranz, U.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 2981-3004. Although the title of this paper included a phrase "katalysielte Umlagerung von Propargyl-phenyläther", the catalytic cycle is less than one, and it is not a catalytic process.
13. (a) Thyagarajan, B. S.; Majumdar, K. C.; Bates, D. K. Heterocycl. Chem. 1975, 12, 59-66. Although the title of this paper includes the phrase "mercuric ion-catalyzed hydration of 1-aryloxy-4-arylthio-2-butynes", the catalytic cycle is less than 1.5, and it is not a practical catalytic process.
14. (b) Bates, D. K.; Jones, M. C. J. Org. Chem. 1978, 43, 3856-3861.
15. Larock, R. C.; Harrison, L. W. J. Am. Chem. Soc. 1984, 106, 4218-4227.
16. (a) Nishizawa, M.; Takenaka, H.; Nishide, H.; Hayashi, Y. Tetrahedron Lett. 1983, 24, 2581-2584.
17. (b) Nishizawa, M.; Morikuni, E.; Asoh, K.; Kan, Y.; Uenoyama, K.; Imagawa, H. Synlett 1995, 169-170.
18. (a) Nishizawa, M.; Takenaka, H.; Hayashi, Y. J. Am. Chem. Soc. 1984, 106, 4290-4291.
19. (b) Nishizawa, M.; Takenaka, H.; Hayashi, Y. J. Org. Chem. 1986, 51, 806.
20. (c) Nishizawa, M.; Yamada, H.; Hayashi, Y. Tetrahedron Lett. 1986, 27, 187-190.
21. (d) Nishizawa, M.; Yamada, H.; Hayashi, Y. J. Org. Chem. 1987, 52, 4878.
22. (e) Nishizawa, M.; Takao, H.; Kanoh, N.; Asoh, K.; Hatakeyama, S.; Yamada, H. Tetrahedron Lett. 1994, 35, 5693-5696.
23. (f) Nishizawa, M.; Morikuni, E.; Takeji, M.; Asoh, K.; Hyodo, I.; Imagawa, H.; Yamada, H. Synlett 1996, 927-928.
24. (g) Nishizawa, M.; Takao, H.; Iwamoto, Y.; Yamada, H.; Imagawa, H. Synlett 1998, 76-78.
25. (h) Nishizawa, M.; Imagawa, H.; Hyodo, I.; Takeji, M.; Morikuni, E.; Asoh, K.; Yamada, H. Tetrahedron Lett. 1998, 39, 389-392
26. (i) Nishizawa, M.; Takao, H.; Iwamoto, Y.; Yamada, H.; Imagawa, H. Synlett 1998, 76-78.
27. (j) Imagawa, H.; Shigaraki, T.; Suzuki, T.; Takao, H.; Yamada, H.; Sugihara, T.; Nishizawa, M. Chem. Pharm. Bull. 1998, 46, 1341-1342.
28. (k) Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T Tetrahedron Lett. 1999, 40, 1153-1156.
29. Nishizawa, M.; Skwarczynski, M.; Imagawa, H.; Sugihara, T. Chem. Lett. 2002, 12-13.
30. Nishizawa, M.; Yadav, V. K.; Skwarczynski, M.; Takao, H.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 1609-1611.
31. 2Hg are extremely dangerous, causing serious damage to the central nervous system, most organomercury compounds with higher molecular weight such as phenylmercuric acetate and mercurochrome have been employed as agrochemicals and medicine, respectively, and are not so toxic.
32. 3-NaCl (1:1) solution, the organic extract was dried and concentrated. Column chromatography of the crude material with hexane and ethyl acetate afforded the product.
33. NMR yield based upon dibromomethane as an internal standard.