Friedel-Crafts acylation of arenes with carboxylic acids using silica gel supported AlCl3

Aromatic compounds react smoothly with carboxylic acids in the presence of silica gel supported aluminium trichloride to afford the corresponding ketones with high regioselectivity in high to excellent yields. The catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency.

Anahtar Kelimeler:

Acylation, aluminium trichloride, ketones, silica gel

Friedel-Crafts acylation of arenes with carboxylic acids using silica gel supported AlCl3

Keywords:

Acylation, aluminium trichloride, ketones, silica gel,

PDF

___

Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195, and references cited therein.
Jensen, R.; Goldman, G. In Friedel-Crafts and Related Reactions, vol. III; Olah, G., Ed.; Wiley Interscience, New York, 1964.
Franck, H. G.; Stadelhofer, J. W. Industrial Aromatic Chemistry, Springer-Verlag, Berlin, 1988.
Hosseini Sarvari, M.; Sharghi, S. J. Org. Chem. 2004, 69, 6953-6956.
Kantam, M. L.; Ranganath, K. V. S.; Sateesh, M.; Kumar, K. B. S.; Choudary, B. M. J. Mol. Catal. A; Chem. , 225, 15-20. Earle, M. J.; Hakala, U.; Hardacre, C.; Karkkainen, J.; McAuley, B. J.; Rooney, D. W.; Seddon, K. R.; Thompson, J. M.; Wahala, K. Chem. Commun. 2005, 903-905.
Gopalakrishnan, M.; Sureshkumar, P.; Kanagarajan, V.; Thanusu, J. Catal. Commun. 2005, 6, 753-756.
Jang, D. O.; Moon, K. S.; Cho, D. H.; Kim, J. G. Tetrahedron Lett. 2006, 47, 6063-6066.
Sartori, G.; Maggi, R. Chem. Rev. 2006, 106, 1077-1104.
Li, C.; Liu, W.; Zhao, Z. Catal. Commun. 2007, 8, 1834-1837.
Zayed, F.; Greiner, L.; Schulz, P. S.; Lapkin, A.; Leitner, W. Chem. Commun. 2008, 79-81. de Noronha, R. G.; Fernandes, A. C.; Romao, C. C. Tetrahedron Lett. 2009, 50, 1407-1410.
Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P. J. Org. Chem. 1986, 51, 2128-2130.
Wang, Q. L.; Ma, Y.; Ji, X.; Yan, H.; Qiu, Q. J. Chem. Soc., Chem. Commun. 1995, 2307-2308.
Ma, Y.; Wang, Q. L.; Jiang, W.; Zuo, B. Appl. Catal. A: General 1997, 165, 199-206.
Kaur, J.; Kozhevnikov, I. V. Chem. Commun. 2002, 2508-2509.
Cui, D. M.; Kawamura, M.; Shimada, S.; Hayashi, T.; Tanaka, M. Tetrahedron Lett. 2003, 44, 4007-4010.
Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F. Tetrahedron 2004, 60, 10843-10850.
Cui, D. M.; Zhang, C.; Kawamura, M.; Shimada, S. Tetrahedron Lett. 2004, 45, 1741-1745.
Hosseini Sarvari, M.; Sharghi, H. Synthesis 2004, 2165-2168.
Kawamura, M.; Cui, D. M.; Shimada, S. Tetrahedron 2006, 62, 9201-9209.
Wagholikar, S. G.; Niphadkar, P. S.; Mayadevi, S.; Sivasanker, S. Appl. Catal. A: General 2007, 317, 250-257.
Khodaei, M. M.; Alizadeh, A.; Nazari E. Tetrahedron Lett. 2007, 48, 4199-4202.
Shimizu, K. I.; Niimi, K.; Satsuma, A. Catal. Commun. 2008, 9, 980-983.
Hajipour, A. R.; Zarei, A.; Khazdooz, L.; Ruoho, A. E. Synth. Commun. 2009, 39, 2702-2722.
Parvanak Borujeni, K.; Tamami, B. Catal. Commun. 2007, 8, 1191-1196.
In the preparation, 1.0 g of solid catalyst was fused with Na metal, extracted with 10 mL of water, and Şltered. The aluminium and chloride content of the Şltrate was determined by the Mohr titration method. For the procedure, refer to: I. M. Kolthoﬀ, E. B. Sandell, Textbook of Quantitative Inorganic Analysis, 3rd ed., Macmillan Company, New York, 1965, pp. 451 and 542.
Paul, S.; Nanda, P.; Gupta, R.; Loupy, A. Synthesis 2003, 2877-2881.
Gopalakrishnan, M.; Sureshkumar, P.; Kanagarajan, V.; Thanusu, J. Catal. Commun. 2005, 6, 753-756.
Desmurs, J. R.; Labrouillere, M.; Roux, C. L.; Gaspard, H.; Laporterie, A.; Dubac, J. Tetrahedron Lett. 1997, 38, 8874.
Kobayashi, S.; Iwamoto, S. Tetrahedron Lett. 1998, 39, 4697-4700.
Chen, X.; Yu, M.; Wang, M. J. Chem. Res. 2005, 80-81.
Chapman, C. J.; Frost, C. G.; Hartley, J. P.; Whittle, A. J. Tetrahedron Lett. 2001, 42, 773-775.
Sasse, A.; Ligneau, X.; Sadek, B.; Elz, S.; Pertz, H. H.; Ganellin, C. R.; Arrang, J. M.; Schwartz, J. C.; Schunack, W.; Stark, H. Arch. Pharm. (Weinheim, Ger.) 2001, 334, 45-52.
Kawada, A.; Mitamura, S.; Kobayashi, S. Synlett 1994, 545-546.
Gatti, N. Tetrahedron Lett. 1990, 31, 3933-3935.
Pivsa-Art, S.; Okura, K.; Miura, M.; Murata, S.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1994, 13, 1703-1706.
Strekowski, L.; Wydra, R. L.; Cegla, M. T.; Czarny, A.; Patterson, S. J. Org. Chem. 1989, 54, 6120-6123.
Kawada, A.; Mitamura, S.; Kobayashi, S. J. Chem. Soc., Chem. Commun. 1996, 183-184.
Nomiya, K.; Sugaya, Y.; Sasa, S.; Miwa, M. Bull. Chem. Soc. Jpn. 1980, 53, 2089-2090.
Cadamuro, S.; Degani, I.; Dughera, S.; Fochi, R.; Gatti, A.; Prandi, C. Gazz. Chim. Ital. 1990, 120, 619-627.
Akg¨un, E.; Pindur, U.; M¨uller, J.;. Heterocycl. Chem. 1983, 20, 1303-1306.
Dictionary of Organic Compounds; 6th Ed., Vol. 9; Chapman and Hall, London, 1996, p. 566.
Miki, Y.; Tsuzaki, Y.; Kai, C.; Hachiken, H. Heterocycles 2002, 57, 1635-1643.