Scandium(III) trifluoromethanesulfonate-catalyzed Friedel-Crafts alkylation of aromatic compounds with secondary alcohol methanesulfonates

Synlett

Volumn , Issue 3, 1998, Pages 255-256

  Kotsuki, Hiyoshizo ^a   Oshisi, Takeshi ^a   Inoue, Motoshi ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 26844571534     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1649     Document Type: Article

References (26)

1. For reviews of Friedel-Crafts alkylation, see: Price, C. C. Org. React., 1946, 3, 1;
2. Olah, G. A. Friedel-Crafts and Related Reactions, Wiley-Interscience: New York, 1964, Vol. II, part 1;
3. Olah, G. A.; Krishnamurti, R.; Prakash, G. K. S. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. III, pp 293-339;
4. March, J. Advanced Organic Chemistry, 4th Ed., Wiley-Interscience: New York, 1992, pp 534-539.
5. Reviews: Kobayashi, S. Synlett 1994, 689;
6. Kobayashi, S. J. Synth. Org. Chem. Jpn. 1995, 53, 370.
7. Kotsuki, H.; Ohishi, T.; Kai, K.; Tatsukawa, A. Unpublished results.
8. See also: Kotsuki, H.; Shimanouchi, T.; Teraguchi, M.; Kataoka, M.; Tatsukawa, A.; Nishizawa, H. Chem. Lett. 1994, 2159.
9. Kronenthal, D. R.; Mueller, R. H.; Kuester, P. L.; Kissick, T. P.; Johnson, E. J. Tetrahedron Lett. 1990, 31, 1241.
10. For related examples: Matsui, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 2663.
11. Matsui, M.; Karibe, N.; Hayashi, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 3569.
12. Tsuchimoto, T.; Hiyama, T.; Fukuzawa, S. Chem. Commun. 1996, 2345.
13. Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. Synlett 1996, 557.
14. Fukuzawa, S.; Tsuchimoto, T.; Hiyama, T. J. Org. Chem. 1997, 62, 151.
15. Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. J. Org. Chem. 1997, 62, 6997.
16. 3 was purchased from Pacific Metals Co., Ltd., Hachinohe, Aomori 031, Japan (FAX: +81-178-22-7350) and used without further purification.
17. 8 and was used repeatedly without a significant loss of activity (2nd run: 89%, 8 h; 3rd run: 83%, 12 h).
18. The contaminating methanesulfonic acid was removed by decantation.
19. 3-catalyzed Friedel-Crafts acylation of anisoles proceeds in quite high yields. See for example: Kawada, A.; Mitamura, S.; Kobayashi, S. Synlett 1994, 545.
20. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153.
21. Kobayashi, S.; Moriwaki, M.; Hachiya, I. J. Chem. Soc., Chem. Commun. 1995, 1527.
22. Kawada, A.; Mitamura, S.; Kobayashi, S. Chem. Commun. 1996, 183.
23. Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Manila, M. Synlett 1996, 171.
24. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull. Chem. Soc. Jpn. 1997, 70, 267.
25. Only a complex hydrocarbon mixture was obtained.
26. These reactions can be also facilitated under TfOH-catalyzed conditions, but this subject will be reported in a forthcoming communication.