Copper(II) acetate promoted oxidative cyclization of arylsulfonyl-o- allylanilines

Organic Letters

Volumn 6, Issue 10, 2004, Pages 1573-1575

  Sherman, Eric S ^a   Chemler, Sherry R ^a   Tan, Tai Boon ^a   Gerlits, Oksana ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; AROMATIC COMPOUND; CESIUM; CESIUM CARBONATE; COPPER ACETATE; SULFONE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; TOSYL 2 ALLYLANILINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; OXIDATION; SULFONYLATION; TEMPERATURE;

EID: 2542624580     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049702+     Document Type: Article

References (24)

1. (a) Hegedus, L. S. In Comprehensive Organic Synthesis; Permagon; New York, 1991; Vol. 4, Chapter 3.1.
2. (b) Hegedus, L. S.; Allen, G. F.; Bozell, J. J.; Waterman, E. L. J. Am. Chem. Soc. 1978, 100, 5800-5807.
3. (c) Fix, S. R.; Brice, J. L.; Stahl, S. S. Angew. Chem., Int. Ed. 2002, 41, 164-166.
4. (a) Rajesawaran, W. G.; Srinivansan, P. C. Synthesis 1994, 270-272.
5. (b) Noto, R.; Gruttadauria, M.; Lo Meo, P.; Frenna, V.; Werber, G. J. Heterocyd. Chem. 1995, 32, 1277.
6. (c) Tsuji, J.; Kezuka, H.; Toshida, Y.; Takayanagi, H.; Yamamoto, K. Tetrahedron 1983, 39, 3279-3282.
7. (d) Coda, A. C.; Desimoni, G.; Monaco, H. L.; Quadrelli, P.; Righetti, P. Gazz. Chim. Ital. 1989, 119, 13-17.
8. (e) Bisiacchi, P.; Coda, A. C.; Desimoni, G.; Righetti, P. P.; Tacconi, G. Gazz. Chim. Ital. 1985, 115, 119-123.
9. (f) Barun, O.; Ila, H.; Junjappa, H.; Singh, O. M. J. Org. Chem. 2000, 65, 1583-1587.
10. (g) Wang, S.-F.; Chuang, C.-P.; Lee, J.-H.; Liu, S.-T. Tetrahedron 1999, 55, 2273-2288.
11. II-catalyzed reactions, see: (a) Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298-5300. (b) Rönn, M.; Bäckvall, J.-E.; Andersson, P. G. Tetrahedron Lett. 1995, 36, 7749-7752. (c) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584-3585. (d) Steinhoff, B. A.; Fix, S. R.; Stahl, S. J. Am. Chem. Soc. 2002, 124, 766-767. (e) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179-4181.
12. II-catalyzed reactions, see: (a) Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298-5300. (b) Rönn, M.; Bäckvall, J.-E.; Andersson, P. G. Tetrahedron Lett. 1995, 36, 7749-7752. (c) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584-3585. (d) Steinhoff, B. A.; Fix, S. R.; Stahl, S. J. Am. Chem. Soc. 2002, 124, 766-767. (e) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179-4181.
13. II-catalyzed reactions, see: (a) Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298-5300. (b) Rönn, M.; Bäckvall, J.-E.; Andersson, P. G. Tetrahedron Lett. 1995, 36, 7749-7752. (c) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584-3585. (d) Steinhoff, B. A.; Fix, S. R.; Stahl, S. J. Am. Chem. Soc. 2002, 124, 766-767. (e) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179-4181.
14. II-catalyzed reactions, see: (a) Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298-5300. (b) Rönn, M.; Bäckvall, J.-E.; Andersson, P. G. Tetrahedron Lett. 1995, 36, 7749-7752. (c) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584-3585. (d) Steinhoff, B. A.; Fix, S. R.; Stahl, S. J. Am. Chem. Soc. 2002, 124, 766-767. (e) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179-4181.
15. II-catalyzed reactions, see: (a) Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298-5300. (b) Rönn, M.; Bäckvall, J.-E.; Andersson, P. G. Tetrahedron Lett. 1995, 36, 7749-7752. (c) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584-3585. (d) Steinhoff, B. A.; Fix, S. R.; Stahl, S. J. Am. Chem. Soc. 2002, 124, 766-767. (e) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179-4181.
16. (a) Ito, R.; Migita, T.; Morikawa, N.; Simamura, O. Tetrahedron 1965, 21, 955.
17. (b) Pryor, W. A.; Davis, W. H., Jr.; Gleaton, J. H. J. Org. Chem. 1975, 40, 2099-2102.
18. (a) Bowman, W. R.; Bridge, C. F.; Brookes, P. J. Chem. Soc., Perkin Trans. 1 2000, 1-14.
19. (b) Zard, S. Z. Synlett 1996, 1148-1154.
20. (c) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543-17594.
21. (d) Gagosz, F.; Moutrille, C.; Zard, S. Z. Org. Lett. 2002, 4, 2707-2709.
22. (e) Broka, C. A.; Eng., K. K. J. Org. Chem. 1986, 51, 5043-5045.
23. (f) See also a recent report using IBX: Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, K. W.; Kanich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233-2244.
24. (g) Studer, A.; Bossart, M. Tetrahedron 2001, 57, 9649-9667.