Niobium pentachloride-silver perchlorate as an efficient catalyst in the Friedel-Crafts acylation and Sakurai-Hosomi reaction of acetals

Tetrahedron

Volumn 61, Issue 19, 2005, Pages 4639-4642

  Arai, Shigeru ^a   Sudo, Yukinori ^a   Nishida, Atsushi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Catalyst; Friedel Crafts acylation; Niobium; Sakurai Hosomi reaction

Indexed keywords

ACETAL DERIVATIVE; AROMATIC COMPOUND; CHLORIDE; NIOBIUM PENTACHLORIDE; PERCHLORATE; SILVER PERCHLORATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; FRIEDEL CRAFTS REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; SAKURAI HOSOMI REACTION; SYNTHESIS;

EID: 17144370898     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.02.061     Document Type: Article

References (35)

1. H. Maeta, T. Nagasawa, Y. Handa, T. Takei, Y. Osamura, and K. Suzuki Tetrahedron Lett. 36 1995 899 902
2. M. Yamamoto, M. Nakazawa, K. Kishikawa, and S. Kohmoto Chem. Commun. 1996 2353 2354
3. J. Howarth, and K. Gillespie Tetrahedron Lett. 37 1996 6011 6012
4. C.K.Z. Andrade, and N.R. Azevedo Tetrahedron Lett. 42 2001 6473 6476
5. C.K.Z. Andrade, and R.A.F. Motos Synlett 2003 1189 1191
6. A. Ortiz, L. Quintero, H. Hernández, S. Maldonado, G. Mendoza, and S. Bernès Tetrahedron Lett. 44 2003 1129 1132
7. Q. Guo, T. Miyaji, R. Hara, B. Shen, and T. Takahashi Tetrahedron 58 2002 7327 7334
8. (b) Quite recently. Kobayashi and co-workers reported a successful example of catalytic asymmetric carbon-carbon bond-forming reaction using a chiral Nb(V) alkoxide, see: Kobayashi, S.; Arai, K.; Shimizu, H.; Ihori, Y.; Ishitani, H.; Yamashita, Y. Angew. Chem., Int. Ed. 2005, 43, 761-764.
9. K. Suzuki, T. Hashimoto, H. Maeta, and T. Matsumoto Synlett 1992 125 128
10. T. Hashimoto, H. Maeta, T. Matsumoto, M. Morooka, S. Ohba, and K. Suzuki Synlett 1992 340 342
11. S. Arai, Y. Sudo, and A. Nishida Synlett 2004 1104 1106
12. For a review of the Friedel-Crafts reaction, see: (a) G.A. Olah Friedel-Crafts Chemistry 1973 Wiley-Interscience London
13. H. Heaney B.M. Trost I. Fleming Comprehensive Organic Synthesis 1991 Pergamon Oxford 733
14. Catalytic Friedel-Crafts acylations using less reactive substrates are reported. See: (a) S. Kobayashi, and S. Iwamoto Tetrahedron Lett. 39 1998 4697 4700
15. M.J. Earle, U. Hakala, B.J. McAuley, M. Nieuwenhuyzen, A. Ramani, and K.R. Seddon Chem. Commun. 2004 1368 1369
16. J.R. Desmurs, M. Labrouillère, C.L. Roux, H. Gaspard, A. Laporterie, and L.J. Dubac Tetrahedron Lett. 38 1997 8871 8874
17. R.P. Singh, R.M. Kamble, K.L. Chandra, C.P. Saravanan, and V.K. Singh Tetrahedron 57 2001 241 247
18. J.P. Hwang, G.K.S. Prakash, and G.A. Olah Tetrahedron Lett. 56 2000 7199 7203
19. C.J. Chapman, C.G. Frost, J.P. Hartley, and A.J. Whittle Tetrahedron Lett. 42 2001 773 775
20. J.-I. Matsuo, K. Odashima, and S. Kobayashi Synlett 2000 403 405
21. I. Hachiya, M. Moriwaki, and S. Kobayashi Bull. Chem. Soc. Jpn. 68 1995 2053 2060
22. Rare earth metal triflates are also efficient catalyst in Friedel-Crafts acylation, see: A. Kawada, S. Mitamura, J.-I. Matsuo, T. Tsuchiya, and S. Kobayashi Bull. Chem. Soc. Jpn. 73 2000 2325 2333 and references cited therein
23. 5-promoted Friedel-Crafts reaction, see: M. Segi, T. Nakajima, and S. Suga Bull. Chem. Soc. Jpn. 53 1980 1465 1466 Ref. 4
24. 3 with a silver salt was one of the most efficient systems in catalytic Friedel-Crafts acylation. See: (a) T. Mukaiyama, T. Ohno, T. Nishimura, S. Suda, and S. Kobayashi Chem. Lett. 1991 1059 1062
25. Various metals with silver salts catalyzed Friedel-Crafts acylation, see: (b) T. Harada, T. Ohno, S. Kobayashi, and T. Mukaiyama Synthesis 1991 1216 1220
26. K. Suzuki, H. Kitagawa, and T. Mukaiyama Bull. Chem. Soc. 66 1993 3729 3734
27. A. Fulstner, D. Voigtländer, W. Schrander, D. Giebel, and M.T. Reetz Org. Lett. 3 2001 417 420
28. K. Ishihara, M. Kubota, H. Kurihara, and H. Yamamoto J. Org. Chem. 61 1996 4560 4567
29. Other examples of direct use of carboxylic acids in Friedel-Crafts acylation. See: (b) M. Kawamura, D.-M. Cui, T. Hayashi, and S. Shimada Tetrahedron Lett. 44 2003 7715 7717
30. H. Firouzabadi, N. Iranpoor, and F. Nowrouzi Tetrahedron Lett. 44 2003 5343 5345
31. B. Chiche, A. Finiels, C. Gauthier, P. Geneste, J. Graille, and D. Pioch J. Org. Chem. 51 1986 2128 2130 and Refs. 1b and 9c
32. For recent examples of the metal-catalyzed Sakurai-Hosomi reaction using acetals, see: (a) T. Watahiki, Y. Akabane, S. Mori, and T. Oriyama Org. Lett. 5 2003 3045 3048
33. L.C. Wieland, H.M. Zerth, and R.S. Mohan Tetrahedron Lett. 43 2002 4597 4600
34. J.S. Yadav, B.V. Subba, and P. Srihari Synlett 2001 673 675
35. 5, see Ref. 1a.