Efficient synthesis of 3-iodoindenes via Lewis-acid catalyzed Friedel-crafts cyclization of iodinated allylic alcohols

Journal of Organic Chemistry

Volumn 73, Issue 10, 2008, Pages 3958-3960

  Zhou, Xiaobo ^a   Zhang, Huimin ^a   Xie, Xin ^a   Li, Yanzhong ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; CATALYST ACTIVITY; CYCLIZATION; DERIVATIVES; FRIEDEL-CRAFTS REACTION; SYNTHESIS (CHEMICAL);

IODINATED ALLYLIC ALCOHOLS; MOLECULAR COMPLEXITY; SUZUKI COUPLING REACTION; SYNTHETIC BUILDING BLOCKS;

ALCOHOLS;

3 IODO 1H INDENE DERIVATIVE; ALLYL ALCOHOL; INDENE DERIVATIVE; IODINE; LEWIS ACID;

ANNULATION REACTION; ARTICLE; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; FRIEDEL CRAFTS REACTION; IODINATION; SUZUKI REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ACIDS; CATALYSIS; CYCLIZATION; HYDROCARBONS, IODINATED; INDENES; MOLECULAR STRUCTURE; PROPANOLS; STEREOISOMERISM;

EID: 43449130082     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800232p     Document Type: Article

References (48)

1. (a) Korach, K. S.; Metzler, M.; McLachlan, J. A. J. Biol. Chem. 1979, 254, 8963.
2. (b) Schneider, M. R.; Ball, H. J. Med. Chem. 1986, 29, 75.
3. (c) Senanayake, C.; Edward Roberts, F.; DiMichele, L.; Ryan, K.; Liu, J.; Fredenburgh, L.; Foster, B. Tetrahedron Lett. 1995, 36, 3993.
4. (d) Harrowven, D. C.; Newman, N. A.; Knight, C. A. Tetrahedron Lett. 1998, 39, 6757.
5. (e) Korte, A.; Legros, J.; Bolm, C. Synlett 2004, 2397. and references therein.
6. (f) Wang, Y.; Mo, S.-Y.; Wang, S.-J.; Li, S.; Yang, Y.-C.; Shi, J.-G. Org. Lett. 2005, 7, 1675.
7. (a) Cadierno, V.; Diez, J.; Pilar, G. M.; Gimeno, J.; Lastra, E. Coord. Chem. Rev. 1999, 193-19, 147.
8. (b) Alt, H. G.; Köppl, A. Chem. Rev. 2000, 100, 1205.
9. (c) Zargarian, D. Coord. Chem. Rev. 2002, 233-234, 157.
10. (d) Leino, R.; Lehmus, P.; Lehtonen, A. Eur. J. Inorg. Chem. 2004, 3201.
11. (a) For reviews, see: Heller, H. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Correy, S.; Ansell, M. F., Eds.; Elsevier: Amsterdam, The Netherlands, 1988; Vol. 3.
12. (b) Okuda, J. Top. Curr. Chem. 1991, 160, 97.
13. (c) Halterman, R. L. Chem. Rev. 1992, 92, 965.
14. (a) Deno, N. C.; Pittman, C.; Turner, J. O. J. Am. Chem. Soc. 1965, 87, 2153.
15. (b) Miller, W.; Pittman, C. J. Org. Chem. 1974, 39, 1955.
16. (c) Olah, G. A.; Asensio, G.; Mayr, H. J. Org. Chem. 1978, 43, 1518.
17. (d) Singh, G.; Ha, H.; Junjappa, H. Synthesis 1986, 744.
18. (e) Pittman, C.; Miller, W. G. J. Am. Chem. Soc. 1973, 95, 2947.
19. (f) Gassman, P. G.; Ray, J. A.; Wenthold, P. G.; Mickelson, J. W. J. Org. Chem. 1991, 56, 5143.
20. (g) Xi, Z.; Guo, R.; Mito, S.; Yan, H.; Kanno, K.; Nakajima, K.; Takahashi, T. J. Org. Chem. 2003, 68, 1252.
21. (h) Hu, Q.; Li, D.; Zhang, H.; Xi, Z. Tetrahedron Lett. 2007, 48, 6167.
22. (a) Battiste, M. A.; Halton, B.; Grubbs, R. H. Chem. Commun. 1967, 907.
23. (b) Parham, W. E.; Egberg, D. C. J. Org. Chem. 1972, 37, 1545.
24. (c) Halton, B.; Kulig, M.; Battiste, M. A.; Perreten, J.; Gibson, D. M.; Griffin, G. W. J. Am. Chem. Soc. 1971, 93, 2327.
25. (d) Padwa, A.; Blacklock, T. J.; Getman, D.; Hatanaka, N. J. Am. Chem. Soc. 1977, 99, 2344.
26. (e) Padwa, A.; Blacklock, T. J.; Loza, R. J. Org. Chem. 1982, 47, 3712.
27. (f) Semmelhack, M. F.; Ho, S.; Cohen, D.; Steigerwald, M.; Lee, M. C.; Lee, G.; Gilbert, A. M.; Wulff, W. D.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7108.
28. Yoshida, H.; Kato, M.; Ogata, T. J. Org. Chem. 1985, 50, 1145.
29. Greifenstein, L. G.; Lambert, J. B.; Nienhuis, R. J.; Fried, H. E.; Pagani, G. A. J. Am. Chem. Soc. 1981, 46, 5125.
30. Zhang, D.; Liu, Z.; Yum, E. K.; Larock, R. C. J. Org. Chem. 2007, 7, 2-251.
31. Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2005, 127, 13498.
32. Odedra, A.; Datta, S.; Liu, R.-S. J. Org. Chem. 2007, 72, 3289.
33. (a) Tutar, A.; Cakmak, O.; Balci, M. Tetrahedron 2001, 57, 9759.
34. (b) Lindley, W. A.; MacDowell, D. W. H. J. Org. Chem. 1982, 47, 705.
35. (c) Ivchenko, N. B.; Ivchenko, P. V.; Nifant'ev, I. E.; Kotov, V. V. Russ. Chem. Bull. 2000, 49, 942.
36. Saito, S.; Homma, M.; Gevorgyan, V.; Yamamoto, Y. Chem. Lett. 2000, 722.
37. (a) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687.
38. (b) Copéret, C.; Negishi, E.; Xi, Z.; Takahashi, T. Tetrahedron Lett. 1994, 35, 695.
39. (c) Zhao, C.; Yu, T.; Xi, Z. Chem. Commun. 2002, 142.
40. (d) Zhao, C.; Yan, J.; Xi, Z. J. Org. Chem. 2003, 68, 4355.
41. (e) Takahashi, T.; Xi, C.; Xi, Z.; Kageyama, M.; Fischer, R.; Nakajima, K.; Negishi, E. J. Org. Chem. 1998, 63, 6802.
42. (f) Copéret, C.; Sugihara, T.; Wu, G.; Shimoyama, I.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 3422.
43. (g) Guo, S.; Zhang, H.; Song, F.; Liu, Y. Tetrahedron 2007, 63, 2009.
44. 2O, see (a) ref 4d.
45. (b) Sun, X.; Izumi, K.; Hu, C.; Lin, G. Chin. J. Chem. 2006, 24, 430.
46. (a) Jordan, V. C. Pharmacol. Rev. 1984, 36, 245.
47. (b) Hong, H. C.; Chamberlain, T. S.; Seiber, K.; Koboldt, C. M.; Isakson, P. C.; Reitz, D. B. Bioorg. Med. Chem. Lett. 1995, 5, 2377.
48. (c) Anstead, G. M.; Peterson, C. S.; Pinney, K. G.; Wilson, S. R.; Katzenellenbogen, J. A. J. Med. Chem. 1990, 33, 2726.