Surprising catalytic activity of bismuth (III) triflate in the Friedel-Crafts acylation reaction

Tetrahedron Letters

Volumn 38, Issue 51, 1997, Pages 8871-8874

  Desmurs, J R ^a   Labrouillere M ^b   Le Roux, C ^b   Gaspard, H ^b   Laporterie, A ^b   Dubac, J ^b  

^a SANOFI   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE;

ACYLATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030830364     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10401-4     Document Type: Article

References (44)

1. (a) Preliminary communication: Le Roux, C; Desmurs, J.R.; Labrouillère, M.; Hernandez, P.; Dubac, J. 9th IUPAC Symposium on Organometallic Chemistry, Göttingen, Germany, July 20-25, 1997, P39;
2. (b) This work has been the subject of patents: Dubac, J.; Gaspard, H.; Labrouillère, M.; Laporterie, A.; Desmurs, J.R. (Rhône-Poulenc Chimie) French Patent 1995, 11250; Dubac, J.; Gaspard, H.; Labrouillère, M.; Laporterie, A.; Desmurs, J.R.; Le Roux, C. (Rhône-Poulenc Chimie) PCT Intern. Appl. WO 97 11,930 (Chem Abstr. 1997, 726, 317246h).
3. (b) This work has been the subject of patents: Dubac, J.; Gaspard, H.; Labrouillère, M.; Laporterie, A.; Desmurs, J.R. (Rhône-Poulenc Chimie) French Patent 1995, 11250; Dubac, J.; Gaspard, H.; Labrouillère, M.; Laporterie, A.; Desmurs, J.R.; Le Roux, C. (Rhône-Poulenc Chimie) PCT Intern. Appl. WO 97 11,930 (Chem Abstr. 1997, 726, 317246h).
4. (b) This work has been the subject of patents: Dubac, J.; Gaspard, H.; Labrouillère, M.; Laporterie, A.; Desmurs, J.R. (Rhône-Poulenc Chimie) French Patent 1995, 11250; Dubac, J.; Gaspard, H.; Labrouillère, M.; Laporterie, A.; Desmurs, J.R.; Le Roux, C. (Rhône-Poulenc Chimie) PCT Intern. Appl. WO 97 11,930 (Chem Abstr. 1997, 726, 317246h).
5. (a) Olah, G.A. Friedel-Crafts Chemistry ; J. Wiley: New York, 1973;
6. (b) Heaney, H. in Comprehensive Organic Synthesis, Trost, B.M. Ed.; Pergamon: Oxford, 1991, Vol. 2, 733-752;
7. (c) Olah, G.; Krishnamurti, R.; Prakash, G.K.S., ibid. 1991, Vol. 3, 293-339; and references therein.
8. (a) Laurent, R. Thèse, Université Paul-Sabatier, 1994, n° 1913;
9. (b) Audhuy-Peaudecerf, M.; Berlan, J.; Dubac, J.; Laporterie, A.; Laurent, R.; Lefeuvre, S. French Patent 1994, 09073.
10. (a) Pearson, D.E.; Buehler, C.A. Synthesis 1972, 533-542;
11. (b) Scheele, J.J. in Electrophilic Aromatic Acylation, Tech. Hogeech, Delft, Neth. 1991; and references cited.
12. (a) Desbois, M.; Gallo, R.; Scuotto, J.F. (Rhône-Poulenc) French Patents 1982, 2,534,905 and 2, 534, 906;
13. (b) Effenberger, F.; Steegmüller, D., Chem. Ber. 1988, 121, 117-123;
14. (c) Effenberger, F.; Steegmüller, D.; Null, V.; Ziegler, T. ibid. 1988, 121, 125-130.
15. Effenberger, F.; Epple, G. Angew. Chem. Int. Ed. 1972, 11, 300-301.
16. (a) Olah, G.A. Angew. Chem. Int. Ed. 1993, 32, 767-788;
17. (b) Yato, M.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1991, 113, 691-692;
18. (c) Sato, Y.; Yato, M.; Ohwada, T.; Saito, S.; Shudo, K. ibid. 1995, 117, 3037-3043.
19. Effenberger, F.; Eberhard, J.K.; Maier, A.H. J. Am. Chem. Soc. 1996, 118, 12572-12579.
20. (a) Mukaiyama, T.; Ohno, T.; Nishimura, T.; Suda, S; Kobayashi, S. Chem. Lett. 1991, 1059;
21. (b) Mukaiyama, T.; Suzuki, K.; Han, J.S.; Kobayashi, S. ibid. 1992, 435-438;
22. (c) Suzuki, K.; Kitagawa, H.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1993, 66, 3729-3734.
23. (a) Cornélis, A.; Gerstmans, A.; Laszlo, P.; Mathy, A.; Zieba, I. Catal. Lett. 1990, 6, 103-109;
24. (b) Cornélis, A.; Laszlo, P.; Wang, S. Tetrahedron Lett. 1993, 34, 3849-3852.
25. (a) Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P.; Graille, J.; Pioch, D. J. Org. Chem. 1986, 51, 2128-2130;
26. (b) Spagnol, M.; Gilbert, L.; Alby, D. Ind. Chem. Libr. 1996, 8 (The Roots of Organic Development); Desmurs, J.R.; Ratton, S., Eds.; Elsevier: Amsterdam; pp. 29-38, and references cited.
27. Pivsa-Art, S.; Okuro, K.; Miura, M.; Murata, S.; Nomura, M. J. Chem. Soc., Perkin Trans 1 1994, 1703-1707.
28. (a) Kawada, A.; Mitamura, S.; Kobayashi, S. J. Chem. Soc., Chem. Commun. 1993, 1157-1158;
29. (b) Kawada, A.; Mitamura, S.; Kobayashi, S. Synlett 1994, 545-546.
30. Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett, 1996, 171-172.
31. Hachiya, I.; Moriwaki, M.; Kobayashi, S. Tetrahedron Lett. 1995, 36, 409-412.
32. Olah, G.A.; Farooq, O.; Morteza, S.; Farnia, F.; Olah, J. J. Am. Chem. Soc. 1988, 770, 2560-2565.
33. Le Roux, C.; Mandrou, S.; Dubac, J. J. Org. Chem. 1996, 61, 3885-3887.
34. Le Roux, C.; Dubac, J. Organometallics 1996, 75, 4646-4648.
35. Labrouillère, M. Thèse, Université Paul-Sabatier, 1995, n° 2133.
36. Dubac, J.; Labrouillère, M.; Laporterie, A. Desmurs, J.R. French Patent 1994, 94.10253; Eur. Pat. Appl. EP 698,593 (Chem. Abstr. 1996, 124, 316758y;
37. Dubac, J.; Labrouillère, M.; Laporterie, A. Desmurs, J.R. French Patent 1994, 94.10253; Eur. Pat. Appl. EP 698,593 (Chem. Abstr. 1996, 124, 316758y;
38. Dubac, J.; Labrouillère, M.; Laporterie, A. Desmurs, J.R. French Patent 1994, 94.10253; Eur. Pat. Appl. EP 698,593 (Chem. Abstr. 1996, 124, 316758y;
39. (b) Desmurs, J.R.; Labrouillère, M.; Dubac, J.; Laporterie, A.; Gaspard, H.; Metz, F. Ind. Chem. Libr. 1996, 8 (The Roots of Organic Development); Desmurs, J.R.; Ratton, S., Eds.; Elsevier: Amsterdam; pp. 15-28.
40. 3. The catalyst used for the reactions described here was mainly the tetrahydrated form.
41. (a) Singh, S.; Verma, A.R.D. Ind. J. Chem. 1983, 22A, 814;
42. (b) Niyogi, D.G.; Singh, S.; Gill, S.; Verma, R.D. J. Fluorine Chem. 1990, 48, 421.
43. Frank, W.; Reiss, G.J.; Schneider, J. Angew. Chem. Int. Ed. 1995, 34, 2416.
44. Louër, M.; Le Roux, C.; Dubac, J. Chem. Mater., in press.