Skip to main content
Log in

Catalytic Friedel–Crafts Acylation of Heteroaromatics

  • Published:
Topics in Catalysis Aims and scope Submit manuscript

Abstract

Catalytic Friedel–Crafts acylation of heteroaromatics has been achieved using metal triflates as catalysts. While conventional Friedel–Crafts acylation often requires the use of more than stoichiometric amounts of aluminum chloride, metal triflates such as tin(II) triflate, scandium triflate, and gallium triflate, etc. have enabled efficient acylation reactions by catalytic use.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. G.A. Olah, Friedel-Crafts and Related Reactions, Vols. I-IV (New York, 1963-1964); G.A. Olah, Friedel-Crafts Chemistry (Wiley-Interscience, New York, 1973); H. Heaney, in: Comprehensive Organic Synthesis, Vol. 2, ed. B.M. Trost (Pergamon Press, Oxford, 1991) pp. 733-752.

  2. D.E. Pearson and C.A. Buehler, Synthesis (1972) 533; F. Effenberger and G.A. Epple, Chem. Int. Ed. Engl. 11 (1972) 300; R.M.G. Roberts and A.R. Sadri, Tetrahedron 39 (1983) 137; F. Effenberger, E. Sohn and G. Epple, Chem. Ber. 116 (1983) 1195; T. Mukaiyama, H. Nagaoka, M. Ohshima and M. Murakami, Chem. Lett. (1986) 165; F. Effenberger and D. Steegmuller, Chem. Ber. 121 (1988) 117; F. Effenberger, D. Steegmuller, V. Null and T. Ziegler, Chem. Ber. 121 (1988) 125; T. Mukaiyama, T. Ohno, T. Nishimura, S. Suda and S. Kobayashi, Chem. Lett. (1991) 1059; T. Harada, T. Ohno, S. Kobayashi and T. Mukaiyama, Synthesis (1991) 1216; T. Mukaiyama, K. Suzuki, J.S. Han and S. Kobayashi, Chem. Lett. (1992) 435; K. Suzuki, H. Kitagawa and T. Mukaiyama, Bull. Chem. Soc. Jpn. 66 (1993) 3729; K. Mikami, O. Kotera, Y. Motoyama, H. Sakaguchi and M. Maruta, Synlett (1996) 171; J. Izumi and T. Mukaiyama, Chem. Lett. (1996) 739; F. Effenberger, J.K. Eberhard and A.H. Maier, J. Am. Chem. Soc. 118 (1996) 12572; J. Nishikido, H. Nakajima, T. Saeki, A. Ishii and K. Mikami, Synlett (1998) 1347.

  3. A. Kawada, S. Mitamura and S. Kobayashi, J. Chem. Soc. Chem. Commun. (1993) 1157; A. Kawada, S. Mitamura and S. Kobayashi, Synlett (1994) 545; A. Kawada, S. Mitamura and S. Kobayashi, Chem. Commun. (1996) 183; J.R. Desmurs, M. Labrouillère, C.L. Roux, H. Gaspard, A. Laporterie and J. Dubac, Tetrahedron Lett. 38 (1997) 8871; S. Répichet, C.L. Roux, J. Dubac and J.-R. Desmurs, Eur. J. Org. Chem. (1998) 2743.

  4. I. Hachiya, M. Moriwaki and S. Kobayashi, Tetrahedron Lett. 36 (1995) 409; I. Hachiya, M. Moriwaki and S. Kobayashi, Bull. Chem. Soc. Jpn. 68 (1995) 2053; S. Kobayashi and S. Iwamoto, Tetrahedron Lett. 39 (1998) 4697; J. Matsuo, K. Odashima and S. Kobayashi, Synlett (2000) 403; S. Kobayashi, I. Komoto and J. Matsuo, Adv. Synth. Catal. 343 (2001) 71.

    Google Scholar 

  5. H.D. Hartough and A.I. Kosak, J. Am. Chem. Soc. 68 (1946) 2639; (b) H.D. Hartough and A.I. Kosak, J. Am. Chem. Soc. 69 (1947) 1012; (c) N.P. Buu-Hoi, N.D. Xuong and N.V. Bac, J. Am. Chem. Soc. 86 (1964) 173; (d) R.X. Xu, H.J. Anderson, N.J. Gogan, C.E. Loader and R. McDonard, Tetrahedron Lett. 22 (1981) 4899; (e) J. Rokach, P. Hamel and M. Kakushima, Tetrahedron Lett. 22 (1981) 4901; (f) M. Kakushima, P. Hamel, R. Frenette and J. Rokach, J. Org. Chem. 48 (1983) 3214; (g) M. Gill, Tetrahedron 40 (1984) 621; (h) G. Simchen and M.W. Majchrzak, Tetrahedron Lett. 26 (1985) 5035; (i) A.P. Kozikowski and A. Ames, Tetrahedron 41 (1985) 4821; (j) S. Scholz, H. Marschall-Weyerstahl and P. Weyerstahl, Liebigs Ann. Chem. (1985) 1935; (k) D.M. Ketcha and G.W. Gribble, J. Org. Chem. 50 (1985) 5451; (l) B.L. Bray, P.H. Mathies, R. Naef, D.R. Solas, T.T. Tidwell, D.R. Artis and J.M. Muchowski, J. Org. Chem. 55 (1990) 6317; (m) S. Cadamuro, I. Degani, S. Dughera, R. Fochi, A. Gatti and L. Piscopo, J. Chem. Soc. Perkin Trans. I (1993) 273; (n) K. Oda, R. Hiratsuka and M. Machida, Heterocycles 43 (1996) 463; (o) A.G.M. Barrett, D.C. Braddock, D. Catterick, D. Chadwick, J.P. Henschke and R.M. McKinnell, Synlett (2000) 847; (p) A. Fürstner, D. Voigtländer, W. Schrader, D. Giebel and M.T. Reetz, Org. Lett. 3 (2001) 417.

    Google Scholar 

  6. N. Ezaki, M. Koyama, T. Shomura, T. Tsuruoka and S. Inoue, J. Antibiol. 36 (1983) 1263; H. Ishibashi, I. Takamuro, Y. Mizukami, M. Irie and M. Ikeda, Synth. Commun. 19 (1989) 443; J.W. Hohhman, D. Dai, B.R. Martin and D.R. Compton, BioMed. Chem. Lett. 4 (1994) 563; G.C. Schloemer, R. Greenhouse and J.M. Muchowski, J. Org. Chem. 59 (1994) 5230; P.J. Loll, D. Picot, O. Ekabo and R.M. Garavito, Biochemistry 35 (1996) 7330; M.Y. Kim, G.J. Lim, J.I. Lim, D.S. Kim, I.Y. Kim and J.S. Yang, Heterocycles 45 (1997) 2041; D.A. Bradley, A.G. Godfrey and C.R. Schmid, Tetrahedron Lett. 40 (1999) 5155; C. Minoletti, S. Dijols, P.M. Dansette and D. Mansuy, Biochemistry 38 (1999) 7828.

    Google Scholar 

  7. S. Kobayashi, I. Hachiya, M. Araki and H. Ishitani, Tetrahedron Lett. 34 (1993) 3755; S. Kobayashi, Synlett. (1994) 689; S. Kobayashi, Eur. J. Org. Chem. (1999) 15.

    Google Scholar 

  8. G.A. Olah, O. Farooq, S.M.F. Farnia and J.A. Olah, J. Am. Chem. Soc. 110 (1988) 2560.

    Google Scholar 

  9. R. Benassi, U. Folli, D. Iarossi, L. Schenetti and F. Taddei, J. Chem. Soc. Perkin Trans. II (1984) 1479.

  10. N. Harada, S. Suzuki, H. Uda and H. Ueno, Chem. Lett. (1972) 803.

  11. J.M. Angelelli, A.R. Katritzky, R.F. Pinzelli and R.D. Topsom, Tetrahedron 28 (1972) 2037.

    Google Scholar 

  12. J.A. Elix and M.V. Sargent, J. Chem. Soc. C (1968) 595.

  13. C.U. Pittman, Jr. and R.M. Hanes, J. Org. Chem. 42 (1977) 1194.

    Google Scholar 

  14. H.-S. Ryang and H. Sakurai, J. Chem. Soc. Chem. Commun. (1972) 77.

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Komoto, I., Matsuo, Ji. & Kobayashi, S. Catalytic Friedel–Crafts Acylation of Heteroaromatics. Topics in Catalysis 19, 43–47 (2002). https://doi.org/10.1023/A:1013829215544

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1013829215544

Navigation