Catalytic direct C-acylation of phenol and naphthol derivatives using carboxylic acids as acylating reagents

Tetrahedron Letters

Volumn 37, Issue 24, 1996, Pages 4183-4186

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

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; KETONE; NAPHTHOL DERIVATIVE; PHENOL DERIVATIVE;

ACYLATION; ARTICLE; CATALYSIS;

EID: 0029891860     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00790-3     Document Type: Article

References (31)

1. (a) Olah, G. A. Friedel-Crafts Chemistry, Wiley-Interscience, New York (1973).
2. (b) Heaney, H. Comprehensive Organic Synthesis, Vol. 2, ed by Trost, B. M. Pergamon Press, Oxford (1991), p. 733-752.
3. (a) Niyazov, A. N.; Namatov, B.; Atlyev, Kh. Izv. Akad. Nauk Turkn. SSR, Ser. Fiz.-Tekh., Khim. Geol. Nauk 1974, 4, 62-66; CA 1975, 82, 170275d.
4. (a) Niyazov, A. N.; Namatov, B.; Atlyev, Kh. Izv. Akad. Nauk Turkn. SSR, Ser. Fiz.-Tekh., Khim. Geol. Nauk 1974, 4, 62-66; CA 1975, 82, 170275d.
5. (b) Niyazov, A. N.; Namatov, B.; Atlyev, Kh. Izv. Akad. Nauk Turkn. SSR, Ser. Fiz.-Tekh., Khim. Geol. Nauk 1974, 6, 65-68; CA, 1975, 83, 58366d.
6. (b) Niyazov, A. N.; Namatov, B.; Atlyev, Kh. Izv. Akad. Nauk Turkn. SSR, Ser. Fiz.-Tekh., Khim. Geol. Nauk 1974, 6, 65-68; CA, 1975, 83, 58366d.
7. (c) Namatov, B.; Atlyev, Kh. Mater. Resp. Nauchno-Tekh. Konf. Molodykh Uch. Pererab. Nefti Neftekhim., 2nd 1974, 166-167; CA 1976, 85, 77796b.
8. (c) Namatov, B.; Atlyev, Kh. Mater. Resp. Nauchno-Tekh. Konf. Molodykh Uch. Pererab. Nefti Neftekhim., 2nd 1974, 166-167; CA 1976, 85, 77796b.
9. (d) Trost, B. M.; Saulnier, M. G. Tetrahedron Lett. 1985, 26, 123-126.
10. (e) Crombie, L.; Jones, R. C. F.; Palmer, C. J. ibid. 1985, 26, 2933-2936.
11. (a) Dorofeenko, G. N.; Tkachenko, V. V. Khim. Geterotsikl. Soedin. 1971, 7, 1703-1704; CA, 1972, 76, 153503k.
12. (a) Dorofeenko, G. N.; Tkachenko, V. V. Khim. Geterotsikl. Soedin. 1971, 7, 1703-1704; CA, 1972, 76, 153503k.
13. (b) Dorofeenko, G. N.; Tkachenko, V. V. Khim. Geterotsikl. Soedin. 1974, 2, 176-180; CA, 1974, 81, 13347r.
14. (b) Dorofeenko, G. N.; Tkachenko, V. V. Khim. Geterotsikl. Soedin. 1974, 2, 176-180; CA, 1974, 81, 13347r.
15. Sartori, G.; Bigi, F. J. Org. Chem. 1990, 55, 4371-4377, and references cited therein.
16. 3. Fodor, G.; Kiss, J.; Szekerke, M. J. Org. Chem. 1950, 15, 227-232; Kindler, K.; Oelschläger, H. Chem. Ber. 1954, 87, 194-202.
17. 3. Fodor, G.; Kiss, J.; Szekerke, M. J. Org. Chem. 1950, 15, 227-232; Kindler, K.; Oelschläger, H. Chem. Ber. 1954, 87, 194-202.
18. Some examples of Friedel-Crafts acylation with carboxylic acids were reported. In most cases, more than stoichiometric amounts of acids were used as promoters. (a) Roberts, R. M. G.; Sadri, A. R. Tetrahedron 1983, 39, 137-142.
19. (b) Hino, M.; Arata, K. J. Chem. Soc., Chem. Commun. 1985, 112-113.
20. (c) Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P. J. Org. Chem. 1986, 51, 2128-2130.
21. (d) Keumi, T.; Yoshimura, K.; Shimada, M.; Kitajima, H. Bull. Chem. Soc. Jpn. 1988, 61, 455-459.
22. Kobayashi, S.; Moriwaki, M.; Hachiya, I. J. Chem. Soc., Chem. Commun. 1995, 1527-1528.
23. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153-1154.
24. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Tetrahedron Lett. 1996, 37, 2053-2056.
25. (a) Hachiya, I.; Moriwaki, M.; Kobayashi, S. Tetrahedron Lett. 1995, 36, 409-412.
26. (b) Hachiya, I.; Moriwaki, M.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1995, 68, 2053-2060.
27. 4 was dissolved in this media.
28. 4 was used.
29. For example, (a) Martin, R. Org. Prep. Proced. Int. 1992, 24, 369-435.
30. (b) Chatterjea, J. N.; Gupta, S. N. P.; Mehrotra, V. N. J. Indian Chem. Soc. 1965, 42, 205-210.
31. (c) Martin, R.; Betoux, J. M.; Coton, G. Bull. Soc. Chim. Fr. 1972, 4694-4698, and references cited therein.