The Catalytic Fries Rearrangement and o-Acylation Reactions Using Group 3 and 4 Metal Triflates as Catalysts

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 1, 1997, Pages 267-273

  Kobayashi, Shü ^a   Moriwaki, Mitsuhiro ^a   Hachiya, Iwao ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000568181     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.267     Document Type: Article

References (69)

1. a) R. Martin, Org. Prep. Proced. Int., 24, 369 (1992).
2. See also, b) T. Yoshino, I. Kijima, M. Sugiura, and T. Shoji, Yuki Gosei Kagaku Kyokai Shi, 21, 463 (1963).
3. a) R. W. Stoughton, J. Am. Chem. Soc., 57, 202 (1935);
4. b) G. Read and V. M. Ruiz, J. Chem. Soc., Perkin Trans. 1, 1973, 235;
5. c) L. Merle-Aubry, D. A. Holden, Y. Merle, and J. E. Guillet, Macromolecules, 13, 1138 (1980);
6. d) T. A. Chorn, R. G. F. Giles, I. R. Green, V. I. Hugo, P. R. K. Mitchell, and S. C. Yorke, J. Chem. Soc., Perkin Trans. 1, 1984, 1339;
7. e) M. A. Rizzacasa and M. V. Sargent, Aust. J. Chem., 41, 1087 (1988).
8. D. J. Crouse, S. L. Hurlbut, and M. S. Wheeler. J. Org. Chem., 46, 374 (1981).
9. a) Y. Takanishi, Y. Ouchi, H. Takezoe, A. Fukuda, A. Mochizuki, and M. Nakatsuka, Mol. Cryst. Liq. Cryst., 199, 111 (1991);
10. b) A. Mochizuki and S. Kobayashi, Mol. Cryst. Liq. Cryst., 243, 77 (1994).
11. A photo-Fries rearrangement has also been developed to overcome the disadvantages of the Lewis acid-promoted reactions. a) D. J. Crouse, S. L. Hurlbut, and M. S. Wheeler, J. Org. Chem., 46, 374 (1981); b) D. Bellus and P. Hrdlovic, Chem. Rev., 67, 599 (1967).
12. A photo-Fries rearrangement has also been developed to overcome the disadvantages of the Lewis acid-promoted reactions. a) D. J. Crouse, S. L. Hurlbut, and M. S. Wheeler, J. Org. Chem., 46, 374 (1981); b) D. Bellus and P. Hrdlovic, Chem. Rev., 67, 599 (1967).
13. The Fries rearrangement is promoted by some protic acids such as hydrofluoric, perchloric, polyphosphoric, and sulfonic acids. Effenberger et al. reported Fries rearrangement of aryl benzoates using a catalytic amount of trifluoromethanesulfonic acid. a) F. Effenberger, H. Klenk, and P. L. Reiter. Angew. Chem., Int. Ed. Engl., 12, 775 (1973); b) F. Effenberger and R. Gutmann, Chem. Ber., 115, 1089 (1982).
14. The Fries rearrangement is promoted by some protic acids such as hydrofluoric, perchloric, polyphosphoric, and sulfonic acids. Effenberger et al. reported Fries rearrangement of aryl benzoates using a catalytic amount of trifluoromethanesulfonic acid. a) F. Effenberger, H. Klenk, and P. L. Reiter. Angew. Chem., Int. Ed. Engl., 12, 775 (1973); b) F. Effenberger and R. Gutmann, Chem. Ber., 115, 1089 (1982).
15. a) A. N. Niyazov, B. Namatov, and Kh. Atlyev, Izv. Akad. Nauk Turkn. SSR, Ser. Fiz.-Tekh., Khim. Geol. Nauk, 1974, (4), 62; Chem. Abstr., 82, 170275d (1975);
16. a) A. N. Niyazov, B. Namatov, and Kh. Atlyev, Izv. Akad. Nauk Turkn. SSR, Ser. Fiz.-Tekh., Khim. Geol. Nauk, 1974, (4), 62; Chem. Abstr., 82, 170275d (1975);
17. b) A. N. Niyazov, B. Namatov, and Kh. Atlyev, Izv. Akad. Nauk Turkn. SSR. Ser. Fiz.-Tekh., Khim. Geol. Nauk, 1974, (6), 65; Chem. Abstr., 83, 58366d (1975);
18. b) A. N. Niyazov, B. Namatov, and Kh. Atlyev, Izv. Akad. Nauk Turkn. SSR. Ser. Fiz.-Tekh., Khim. Geol. Nauk, 1974, (6), 65; Chem. Abstr., 83, 58366d (1975);
19. c) B. Namatov and Kh. Atlyev, "Mater. Resp. Nauchno-Tekh. Konf. Molodykh Uch. Pererab. Nefti Neftekhim.," 2nd ed. 1974, p. 166; Chem. Abstr., 85, 77796b (1976);
20. c) B. Namatov and Kh. Atlyev, "Mater. Resp. Nauchno-Tekh. Konf. Molodykh Uch. Pererab. Nefti Neftekhim.," 2nd ed. 1974, p. 166; Chem. Abstr., 85, 77796b (1976);
21. d) B. M. Trost and M. G. Saulnier, Tetrahedron Lett., 26, 123 (1985);
22. e) L. Crombie, R. C. F. Jones, and C. J. Palmer, Tetrahedron Lett., 26, 2933 (1985).
23. a) G.N. Dorofeenko and V. V. Tkachenko, Khim. Geterotsikl. Soedin., 7 (12), 1703 (1971); Chem. Abstr., 76, 153503k (1972);
24. a) G.N. Dorofeenko and V. V. Tkachenko, Khim. Geterotsikl. Soedin., 7 (12), 1703 (1971); Chem. Abstr., 76, 153503k (1972);
25. b) G. N. Dorofeenko and V. V. Tkachenko, 1974, (2), 176; Chem. Abstr., 81, 13347r (1974).
26. o-Acylation of phenols via phenol salts under basic conditions has been reported. G. Sartori and F. Bigi, J. Org. Chem., 55, 4371 (1990), and references cited therein.
27. 2: j) E. J. Corey and K. Shimoji, J. Am. Chem. Soc, 105, 1662 (1983).
28. 2: j) E. J. Corey and K. Shimoji, J. Am. Chem. Soc, 105, 1662 (1983).
29. 2: j) E. J. Corey and K. Shimoji, J. Am. Chem. Soc, 105, 1662 (1983).
30. 2: j) E. J. Corey and K. Shimoji, J. Am. Chem. Soc, 105, 1662 (1983).
31. 2: j) E. J. Corey and K. Shimoji, J. Am. Chem. Soc, 105, 1662 (1983).
32. 2: j) E. J. Corey and K. Shimoji, J. Am. Chem. Soc, 105, 1662 (1983).
33. 2: j) E. J. Corey and K. Shimoji, J. Am. Chem. Soc, 105, 1662 (1983).
34. 2: j) E. J. Corey and K. Shimoji, J. Am. Chem. Soc, 105, 1662 (1983).
35. 2: j) E. J. Corey and K. Shimoji, J. Am. Chem. Soc, 105, 1662 (1983).
36. 2: j) E. J. Corey and K. Shimoji, J. Am. Chem. Soc, 105, 1662 (1983).
37. a) S. Kobayashi, Synlett, 1994, 689;
38. b) S. Kobayashi, H. Ishitani, I. Hachiya, and M. Araki, Tetrahedron, 50, 11623 (1994);
39. c) S. Kobayashi, M. Araki, H. Ishitani, S, Nagayama, and I. Hachiya, Synlett, 1995, 233;
40. d) S. Kobayashi, H. Ishitani, and S. Nagayama, Chem. Lett., 1995, 423;
41. e) S. Kobayashi, M. Araki, and M. Yasuda, Tetrahedron Lett., 36, 5773 (1995);
42. f) S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379;
43. g) S. Kobayashi, H. Ishitani, and S. Nagayama, Synthesis, 1995, 1190;
44. h) H. Ishitani, S. Nagayama, and S. Kobayashi, J. Org. Chem., 61, 1902 (1996);
45. i) S. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu, and A. R. Katritzky, Tetrahedron Lett., 37, 3731 (1996).
46. a) S. Kobayashi, M. Moriwaki, and I. Hachiya, J. Chem. Soc., Chem. Commun., 1995, 1527;
47. b) S. Kobayashi, M. Moriwaki, and I. Hachiya, Synlett. 1995, 1153;
48. c) S. Kobayashi and S. Nagayama, J. Org. Chem., 61, 2256 (1996);
49. d) S. Kobayashi, I. Hachiya, S. Suzuki, and M. Moriwaki, Tetrahedron Lett., 37, 2809 (1996);
50. e) S. Kobayashi, I. Hachiya, and M. Yasuda, Tetrahedron Lett., 37, 5569 (1996);
51. f) S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., in press. See also, Ref. 14.
52. a.) I. Hachiya, M. Moriwaki, and S. Kobayashi, Tetrahedron Lett., 36, 409 (1995);
53. b) I. Hachiya, M. Moriwaki, and S. Kobayashi, Bull. Chem. Soc. Jpn., 68, 2053 (1995).
54. 3 is also an effective catalyst for the Friedel-Crafts acylation. a) A. Kawada, S, Mitamura, and S. Kobayashi, Synlett, 1994, 545; b) A. Kawada, S. Mitamura, and S. Kobayashi, J. Chem. Soc., Chem. Commun., 1996, 183.
55. 3 is also an effective catalyst for the Friedel-Crafts acylation. a) A. Kawada, S, Mitamura, and S. Kobayashi, Synlett, 1994, 545; b) A. Kawada, S. Mitamura, and S. Kobayashi, J. Chem. Soc., Chem. Commun., 1996, 183.
56. Preliminary communication: a) S. Kobayashi, M. Moriwaki, and I. Hachiya, J. Chem. Soc., Chem. Commun., 1995, 1527; b) S. Kobayashi, M. Moriwaki, and I. Hachiya, Synlett, 1995, 1153; c) S. Kobayashi, M. Moriwaki, and I. Hachiya, Tetrahedron Lett., 37, 2063 (1996).
57. Preliminary communication: a) S. Kobayashi, M. Moriwaki, and I. Hachiya, J. Chem. Soc., Chem. Commun., 1995, 1527; b) S. Kobayashi, M. Moriwaki, and I. Hachiya, Synlett, 1995, 1153; c) S. Kobayashi, M. Moriwaki, and I. Hachiya, Tetrahedron Lett., 37, 2063 (1996).
58. Preliminary communication: a) S. Kobayashi, M. Moriwaki, and I. Hachiya, J. Chem. Soc., Chem. Commun., 1995, 1527; b) S. Kobayashi, M. Moriwaki, and I. Hachiya, Synlett, 1995, 1153; c) S. Kobayashi, M. Moriwaki, and I. Hachiya, Tetrahedron Lett., 37, 2063 (1996).
59. It was reported that titanium has up to three OTf ligands, probably due to its small ionic radius. a) M. Schmeiber, P. Sartori, and B. Lippsmeiser, Chem. Ber., 103, 863 (1970); b) Y. Tanabe and T. Mukaiyama, Chem. Lett., 1984, 1867; c) Y. Tanabe, Bull. Chem. Soc. Jpn., 67, 3309 (1994); d) J. Izumi, I. Shiina, and T. Mukaiyama, Chem. Lett., 1995, 141.
60. It was reported that titanium has up to three OTf ligands, probably due to its small ionic radius. a) M. Schmeiber, P. Sartori, and B. Lippsmeiser, Chem. Ber., 103, 863 (1970); b) Y. Tanabe and T. Mukaiyama, Chem. Lett., 1984, 1867; c) Y. Tanabe, Bull. Chem. Soc. Jpn., 67, 3309 (1994); d) J. Izumi, I. Shiina, and T. Mukaiyama, Chem. Lett., 1995, 141.
61. It was reported that titanium has up to three OTf ligands, probably due to its small ionic radius. a) M. Schmeiber, P. Sartori, and B. Lippsmeiser, Chem. Ber., 103, 863 (1970); b) Y. Tanabe and T. Mukaiyama, Chem. Lett., 1984, 1867; c) Y. Tanabe, Bull. Chem. Soc. Jpn., 67, 3309 (1994); d) J. Izumi, I. Shiina, and T. Mukaiyama, Chem. Lett., 1995, 141.
62. It was reported that titanium has up to three OTf ligands, probably due to its small ionic radius. a) M. Schmeiber, P. Sartori, and B. Lippsmeiser, Chem. Ber., 103, 863 (1970); b) Y. Tanabe and T. Mukaiyama, Chem. Lett., 1984, 1867; c) Y. Tanabe, Bull. Chem. Soc. Jpn., 67, 3309 (1994); d) J. Izumi, I. Shiina, and T. Mukaiyama, Chem. Lett., 1995, 141.
63. For example: a) J. N. Chatterjea, S. N. P. Gupta, and V. N. Mehrotra, J. Indian Chem. Soc., 42, 205 (1965); b) R. Martin, J. M. Betoux, and G. Coton, Bull. Soc. Chim. Fr., 1972, 4319, and references cited therein.
64. For example: a) J. N. Chatterjea, S. N. P. Gupta, and V. N. Mehrotra, J. Indian Chem. Soc., 42, 205 (1965); b) R. Martin, J. M. Betoux, and G. Coton, Bull. Soc. Chim. Fr., 1972, 4319, and references cited therein.
65. K. Ishihara, M. Kubota, H. Kurihara, and H. Yamamoto, J. Am. Chem. Soc., 117, 4413 (1995).
66. S. Kobayashi, M. Moriwaki, and I. Hachiya, Tetrahedron Lett., 37, 4183 (1996).
67. a) K. F. Thom, U. S. Patent 3615169 (1971); Chem. Abstr., 76, 5436a (1972);
68. a) K. F. Thom, U. S. Patent 3615169 (1971); Chem. Abstr., 76, 5436a (1972);
69. b) S. Kobayashi, I. Hachiya, M. Araki, and H. Ishitani, Tetrahedron Lett., 34, 3755 (1993).