Lewis acid-catalyzed Friedel-Crafts acylation reaction using carboxylic acids as acylating agents

Tetrahedron Letters

Volumn 44, Issue 42, 2003, Pages 7715-7717

  Kawamura, Masato ^a   Cui, Dong Mei ^a   Hayashi, Teruyuki ^a   Shimada, Shigeru ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

Carboxylic acid; Friedel Crafts acylation; Lewis acid; Rare earth metal

Indexed keywords

ALIPHATIC AMINE; CARBOXYLIC ACID DERIVATIVE; EUROPIUM; LANTHANIDE; LEWIS ACID;

ARTICLE; CATALYSIS; CATALYST; FRIEDEL CRAFTS REACTION; HIGH TEMPERATURE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0141682302     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.099     Document Type: Article

References (27)

1. Olah, G. A. Friedel-Crafts and Related Reactions; Wiley-Interscience: New York, 1964; Vol. III, Part 1.
2. Chiche B., Finiels A., Gauthier C., Geneste P. J. Org. Chem. 51:1986;2128-2130.
3. Gauthier C., Chiche B., Finiels A., Geneste P. J. Mol. Catal. 50:1989;219-229.
4. Wang Q. L., Ma Y., Ji X., Yan H., Qiu Q. J. Chem. Soc., Chem. Commun. 1995;2307-2308.
5. Singh A. P., Pandey A. K. J. Mol. Catal. A. 123:1997;141-147.
6. Pandey A. K., Singh A. P. Catal. Lett. 44:1997;129-133.
7. De Castro C., Primo J., Corma A. J. Mol. Catal. A. 134:1998;215-222.
8. Izumi Y., Ogawa M., Nohara W., Urabe K. Chem. Lett. 1992;1987-1990.
9. Kaur J., Kozhevnikov I. V. Chem. Commun. 2002;2508-2509.
10. Chiche B., Finiels A., Gautheir C., Geneste P. J. Mol. Catal. 42:1987;229-235.
11. Suzuki K., Kitagawa H., Mukaiyama T. Bull. Chem. Soc. Jpn. 66:1993;3729-3734.
12. Kobayashi S., Moriwaki M., Hachiya I. Tetrahedron Lett. 37:1996;4183-4186.
13. For recent examples of Friedel-Crafts acylation with acid chlorides or acid anhydrides as acylating agents using a catalytic amount of Lewis acids, see: (a) Kawada, A.; Mitamura, S.; Matsuo, J.; Tsuchiya, T.; Kobayashi, S. Bull. Chem. Soc. Jpn. 2000, 73, 2325-2333; (b) Singh, R. P.; Kamble, R. M.; Chandra, K. L.; Saravanan, P.; Singh, V. K. Tetrahedron 2001, 57, 241-247; (c) Duris, F. ; Barbier-Baudry, D.; Dormond, A.; Desmurs, J. R.; Bernard, J. M. J. Mol. Catal. A 2002, 188, 97-104; (d) Le Roux, C.; Dubac, J. Synlett 2002, 181-200; (e) Prakash, G. K. S.; Yan, P.; Torok, B.; Bucsi, I.; Tanaka, M.; Olah, G. A. Catal. Lett. 2003, 85, 1-6.
14. For recent examples of Friedel-Crafts acylation with acid chlorides or acid anhydrides as acylating agents using a catalytic amount of Lewis acids, see: (a) Kawada, A.; Mitamura, S.; Matsuo, J.; Tsuchiya, T.; Kobayashi, S. Bull. Chem. Soc. Jpn. 2000, 73, 2325-2333; (b) Singh, R. P.; Kamble, R. M.; Chandra, K. L.; Saravanan, P.; Singh, V. K. Tetrahedron 2001, 57, 241-247; (c) Duris, F. ; Barbier-Baudry, D.; Dormond, A.; Desmurs, J. R.; Bernard, J. M. J. Mol. Catal. A 2002, 188, 97-104; (d) Le Roux, C.; Dubac, J. Synlett 2002, 181-200; (e) Prakash, G. K. S.; Yan, P.; Torok, B.; Bucsi, I.; Tanaka, M.; Olah, G. A. Catal. Lett. 2003, 85, 1-6.
15. For recent examples of Friedel-Crafts acylation with acid chlorides or acid anhydrides as acylating agents using a catalytic amount of Lewis acids, see: (a) Kawada, A.; Mitamura, S.; Matsuo, J.; Tsuchiya, T.; Kobayashi, S. Bull. Chem. Soc. Jpn. 2000, 73, 2325-2333; (b) Singh, R. P.; Kamble, R. M.; Chandra, K. L.; Saravanan, P.; Singh, V. K. Tetrahedron 2001, 57, 241-247; (c) Duris, F. ; Barbier-Baudry, D.; Dormond, A.; Desmurs, J. R.; Bernard, J. M. J. Mol. Catal. A 2002, 188, 97-104; (d) Le Roux, C.; Dubac, J. Synlett 2002, 181-200; (e) Prakash, G. K. S.; Yan, P.; Torok, B.; Bucsi, I.; Tanaka, M.; Olah, G. A. Catal. Lett. 2003, 85, 1-6.
16. For recent examples of Friedel-Crafts acylation with acid chlorides or acid anhydrides as acylating agents using a catalytic amount of Lewis acids, see: (a) Kawada, A.; Mitamura, S.; Matsuo, J.; Tsuchiya, T.; Kobayashi, S. Bull. Chem. Soc. Jpn. 2000, 73, 2325-2333; (b) Singh, R. P.; Kamble, R. M.; Chandra, K. L.; Saravanan, P.; Singh, V. K. Tetrahedron 2001, 57, 241-247; (c) Duris, F. ; Barbier-Baudry, D.; Dormond, A.; Desmurs, J. R.; Bernard, J. M. J. Mol. Catal. A 2002, 188, 97-104; (d) Le Roux, C.; Dubac, J. Synlett 2002, 181-200; (e) Prakash, G. K. S.; Yan, P.; Torok, B.; Bucsi, I.; Tanaka, M.; Olah, G. A. Catal. Lett. 2003, 85, 1-6.
17. For recent examples of Friedel-Crafts acylation with acid chlorides or acid anhydrides as acylating agents using a catalytic amount of Lewis acids, see: (a) Kawada, A.; Mitamura, S.; Matsuo, J.; Tsuchiya, T.; Kobayashi, S. Bull. Chem. Soc. Jpn. 2000, 73, 2325-2333; (b) Singh, R. P.; Kamble, R. M.; Chandra, K. L.; Saravanan, P.; Singh, V. K. Tetrahedron 2001, 57, 241-247; (c) Duris, F. ; Barbier-Baudry, D.; Dormond, A.; Desmurs, J. R.; Bernard, J. M. J. Mol. Catal. A 2002, 188, 97-104; (d) Le Roux, C.; Dubac, J. Synlett 2002, 181-200; (e) Prakash, G. K. S.; Yan, P.; Torok, B.; Bucsi, I.; Tanaka, M.; Olah, G. A. Catal. Lett. 2003, 85, 1-6.
18. Walker, M. US Patent 5,362,375, 2002; Chem. Abstr. 2002, 136, 262987.
19. For a recent review on rare-earth metal Lewis acids in organic synthesis, see: Kobayashi S., Sugiura M., Kitagawa H., Lam W. W. Chem. Rev. 102:2002;2227-2302.
20. We have recently reported Lewis acid-catalyzed intramolecular Friedel-Crafts cyclization of 4-arylbutyric acids to form 1-tetralones, see: Cui D.-M., Kawamura M., Shimada S., Hayashi T., Tanaka M. Tetrahedron Lett. 44:2003;4007-4010.
21. 6: C, 7.26; F, 34.46; N, 4.23. Found: C, 7.15; F, 33.92; N, 4.36.
22. Ishihara K., Kubota M., Yamamoto H. Synlett. 1996;265-266.
23. Mikami K., Kotera O., Motoyama Y., Tanaka M. Inorg. Chem. Commun. 1:1998;10-11.
24. Picot A., Repicheta S., Le Roux C., Dubac J., Roques N. J. Fluorine Chem. 116:2002;129-134.
25. 4 and concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/EtOAc=27/1) to give 1-(2,5-dimethylphenyl)-1-octanone as a pale yellow oil (109 mg, 80% yield).
26. For successful examples of less reactive aromatic compounds, see: (a) Kobayashi, S.; Iwamoto, S. Tetrahedron Lett. 1998, 39, 4697-4700; (b) Ref. 6e.
27. For successful examples of less reactive aromatic compounds, see: (a) Kobayashi, S.; Iwamoto, S. Tetrahedron Lett. 1998, 39, 4697-4700; (b) Ref. 6e.