Scandium(III) Triflate-Catalyzed Friedel-Crafts Alkylation Reactions

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6997-7005

  Tsuchimoto, Teruhisa ^a   Tobita, Kazuo ^b   Hiyama, Tamejiro ^a   Fukuzawa, Shin Ichi ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b CHUO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000284687     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970599u     Document Type: Article

References (67)

1. Olah, G. A. Friedel-Crafts and Related Reactions; Wiley-Interscience: New York, 1964; Vol. II, Part 1.
2. Roberts, R. M.; Khalaf, A. A. Friedel-Crafts Alkylation Chemistry. A Century of Discovery, Dekker: New York, 1984.
3. Olah, G. A.; Krishnamurti, R.; Prakash, G. K. S. Friedel-Crafts Alkylations in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991.
4. For a pharmacologically important intramolecular Friedel-Crafts benzylation reaction, see; Yamamoto, T.; Fukumoto, M.; Sakaue, N.; Furusawa, T.; Tashiro, M. Synthesis 1991, 699.
5. (a) Forsberg, J. H.; Spaziano, V. T.; Balasubramanian, T. M.; Liu, G. K.; Kinsley, S. A.; Duckworth, C. A.; Poteruca, J. J.; Brown, P. S.; Miller, J. L. J. Org. Chem. 1987, 52, 1017.
6. (b) Collins, S.; Hong, Y. Tetrahedron Lett. 1987, 28, 4391.
7. (c) Almasio, M.-C.; Arnaud-Neu, F.; Schwing-Weill, M.-J. Helv. Chim. Acta 1983, 66, 1296.
8. (a) Kobayashi, S. Chem. Lett. 1991, 2187.
9. (b) Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625.
10. (c) Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958.
11. (d) Kobayashi, S.; Ishitani, H. J. Chem. Soc., Chem. Commun. 1995, 1379.
12. (e) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975.
13. (f) Fujiwara, K.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1995, 36, 8063.
14. (g) Depu, C.; Libing, Y.; Peng, G. W. Tetrahedron Lett. 1996, 37, 4467.
15. (h) Kotsuki, H.; Teraguchi, M.; Shimomoto, N.; Ochi, M. Tetrahedron Lett. 1996, 37, 3727.
16. For reviews, see: (a) Kobayashi, S. Synlett 1994, 689. (b) Marshman, R. W. Aldrichimica Acta 1995, 28, 77.
17. For reviews, see: (a) Kobayashi, S. Synlett 1994, 689. (b) Marshman, R. W. Aldrichimica Acta 1995, 28, 77.
18. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
19. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
20. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
21. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
22. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
23. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
24. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
25. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
26. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
27. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
28. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
29. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
30. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
31. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
32. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
33. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
34. For selected references on some organic reactions using lanthanide(III) triflate, see: (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815. (b) Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791. (c) Kobayashi, S.; Hachiya, H.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (e) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083. (f) Meguro, M; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597. (g) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (i) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. (j) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (k) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413. (l) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423. (m) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773. (n) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839. (o) Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491. (p) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (q) El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett, 1996, 871.
35. 3 is also applicable to the combinatorial synthesis; see: Kobayashi, S.; Moriwaki, M.; Akiyama, R.; Suzuki, S.; Hachiya, I. Tetrahedron Lett. 1996, 37, 7783.
36. 3 as the catalyst: (a) Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. Synlett 1996, 557. (b) Tsuchimoto, T.; Hiyama, T.; Fukuzawa, S. Chem. Commun. 1996, 2345.
37. 3 as the catalyst: (a) Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. Synlett 1996, 557. (b) Tsuchimoto, T.; Hiyama, T.; Fukuzawa, S. Chem. Commun. 1996, 2345.
38. Mine, N.; Fujiwara, Y.; Taniguchi, H. Chem Lett. 1986, 357.
39. Olah, G. A.; Farooq, O.; Famia, S. M. F.; Olah, J. A. J. Am. Chem. Soc. 1988, 110, 2560.
40. 3 as a catalyst scarcely takes place. (a) Kawada, A.; Mitamura, S.; Kobayashi, S. J. Chem. Soc., Chem. Commun. 1993, 1157; 1996, 183; Synlett 1994, 545. (b) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull Chem. Soc. Jpn. 1997, 70, 267.
41. 3 as a catalyst scarcely takes place. (a) Kawada, A.; Mitamura, S.; Kobayashi, S. J. Chem. Soc., Chem. Commun. 1993, 1157; 1996, 183; Synlett 1994, 545. (b) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull Chem. Soc. Jpn. 1997, 70, 267.
42. 3 as a catalyst scarcely takes place. (a) Kawada, A.; Mitamura, S.; Kobayashi, S. J. Chem. Soc., Chem. Commun. 1993, 1157; 1996, 183; Synlett 1994, 545. (b) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull Chem. Soc. Jpn. 1997, 70, 267.
43. 3 as a catalyst scarcely takes place. (a) Kawada, A.; Mitamura, S.; Kobayashi, S. J. Chem. Soc., Chem. Commun. 1993, 1157; 1996, 183; Synlett 1994, 545. (b) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull Chem. Soc. Jpn. 1997, 70, 267.
44. 3. (a) Olah, G. A.; Kobayashi, S.; Tashiro, M. J. Am. Chem. Soc. 1972, 94, 7448. (b) Olah, G. A.; Olah, J. A. J. Am. Chem. Soc. 1984, 106, 5248.
45. 3. (a) Olah, G. A.; Kobayashi, S.; Tashiro, M. J. Am. Chem. Soc. 1972, 94, 7448. (b) Olah, G. A.; Olah, J. A. J. Am. Chem. Soc. 1984, 106, 5248.
46. Solid superacid-catalyzed benzylation reaction induces the formation of the dehydration products as a byproduct. Yamamoto, T.; Hideshima, C.; Prakash, G. K. S.; Olah, G. A. J. Org. Chem. 1991, 56, 2089.
47. Roberts, R. M.; EI-Khawaga, A. M.; Sweeney, K. M.; EI-Zohry, M. F. J. Org. Chem. 1987, 52, 1959 and references cited therein.
48. Griepentrog, H. Ber. Dtsch. Chem. Ges. 1886, 79, 1876.
49. Saito, S.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1995, 117, 11081.
50. Olah, G. A.; Rasul, G.; York, C.; Prakash, G. K. S. J. Am. Chem. Soc. 1995, 117, 11211 and references cited therein.
51. (a) Hashimoto, Y.; Hirata, K.; Kihara, N.; Hasegawa, M.; Saigo, K. Tetrahedron Lett. 1992, 33, 6351.
52. (b) Hashimoto, Y.; Hirata, K.; Kagoshima, H.; Kihara, N.; Hasegawa, M.; Saigo, K. Tetrahedron 1993, 49, 5969.
53. Climent, M. J.; Corma, A.; Garceía, H.; Primo, J. J. Catal. 1991, 130, 138.
54. Fukuzawa, S.; Tsuchimoto, T.; Hotaka, T.; Hiyama, T. Synlett 1995, 1077.
55. Fukuzawa, S.; Tsuchimoto, T.; Hiyama, T. J. Org. Chem. 1997, 62, 151.
56. (a) DeHaan, F. P.; Delker, G. L.; Covey, W. D.; Ahn, J.; Anksman, M. S.; Brehm, E. C.; Chang, J.; Chicz, R. M.; Cowan, R. L.; Ferrara, D. M.; Fong, C. H.; Harper, J. D.; Irani, C. D.; Kim, J. Y.; Meinhold, R. W.; Miller, K. D.; Roberts, M. P.; Stoler, E. M.; Suh, Y. J.; Tang, M.; Williams, E. L. J. Am. Chem. Soc. 1984, 106, 7038.
57. (b) DeHaan, F. P.; Chan, W. H.; Chang, J.; Cheng, T. B.; Chiriboga, D. A.; Irving, M. M.; Kaufman, C. R.; Kim, G. Y.; Kumar, A.; Na, J.; Nguyen, T. T.; Nguyen, D. T.; Patel, B. R.; Sarin, N. P.; Tidwell, J. H. J. Am. Chem. Soc. 1990, 112, 356.
58. The hydride ion transfer from alkoxy carbon of tetrahydrofuran, 1,3-dioxolane, and 1,3-dioxepane to a trityl cation has been reported. Din, K-u.; Plesch, P. H. J. Chem. Soc., Perkin Trans. 2 1987, 937.
59. Oxidation product of alkyl group could not be detected because it may undergo a condensation reaction to form polymeric products.
60. Effenberger, F.; Günther, G.; Bäuerle, P. Chem. Ber. 1992, 125, 941.
61. Bandaranayake, W. M.; Riggs, N. V. Aust. J. Chem. 1981, 34, 115.
62. The allylation products were identified by comparison to their spectral data with those of authentic samples, (a) Alexakis, A.; Cahiez, G.; Normant, J. F. Synthesis 1979, 826.
63. (b) Hayashi, T.; Konishi, M.; Yokota, K.; Kumada, M. J. Organometal. Chem. 1985, 285, 359.
64. (c) Zadok, E.; Rubinraut, S.; Mazur, Y. J. Org. Chem. 1987, 52, 385.
65. Roelofsen, D. P.; van Bekkum, H. Synthesis 1972, 419.
66. Napolitano, E.; Fiaschi, R.; Mastrorilli, E. Synthesis 1986, 122.
67. Eliel, E. L.; Badding, V. D.; Rerick, M. N. J. Am. Chem. Soc. 1962, 84, 2371.