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

被引:49
作者
Arai, S [1 ]
Sudo, Y [1 ]
Nishida, A [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
关键词
catalyst; Friedel-Crafts acylation; niobium; Sakurai-Hosomi reaction;
D O I
10.1016/j.tet.2005.02.061
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Friedel-Crafts acylation catalyzed by niobium pentachloride with silver salt is described. Aromatic compounds with Ac2O or Bz(2)O were smoothly converted into the corresponding ketones in good to excellent yields. This system was also applied to the Sakurai-Hosomi reaction using acetals. The reaction proceeded quite rapidly to give the desired products in excellent yields. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4639 / 4642
页数:4
相关论文
共 34 条
  • [1] Niobium(V) chloride-mediated allylation of aldehydes. Scope and stereoselectivity
    Andrade, CKZ
    Azevedo, NR
    [J]. TETRAHEDRON LETTERS, 2001, 42 (37) : 6473 - 6476
  • [2] ANDRADE CKZ, 2001, SYNLETT, P1089
  • [3] A simple and regioselective carbon-oxygen bond cleavage using niobium(V)
    Arai, S
    Sudo, Y
    Nishida, A
    [J]. SYNLETT, 2004, (06) : 1104 - 1106
  • [4] Efficient aromatic and heteroatom acylations using catalytic indium complexes with lithium perchlorate
    Chapman, CJ
    Frost, CG
    Hartley, JP
    Whittle, AJ
    [J]. TETRAHEDRON LETTERS, 2001, 42 (05) : 773 - 775
  • [5] FRIEDEL-CRAFTS ACYLATION OF TOLUENE AND PARA-XYLENE WITH CARBOXYLIC-ACIDS CATALYZED BY ZEOLITES
    CHICHE, B
    FINIELS, A
    GAUTHIER, C
    GENESTE, P
    GRAILLE, J
    PIOCH, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (11) : 2128 - 2130
  • [6] Surprising catalytic activity of bismuth (III) triflate in the Friedel-Crafts acylation reaction
    Desmurs, JR
    Labrouillere, M
    LeRoux, C
    Gaspard, H
    Laporterie, A
    Dubac, J
    [J]. TETRAHEDRON LETTERS, 1997, 38 (51) : 8871 - 8874
  • [7] Metal bis{(trifluoromethyl)sulfonyl}amide complexes: highly efficient Friedel-Crafts acylation catalysts
    Earle, MJ
    Hakala, U
    McAuley, BJ
    Nieuwenhuyzen, M
    Ramani, A
    Seddon, KR
    [J]. CHEMICAL COMMUNICATIONS, 2004, (12) : 1368 - 1369
  • [8] Solvent-free Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the presence of trifluoroacetic anhydride and aluminum dodecatungstophosphate
    Firouzabadi, H
    Iranpoor, N
    Nowrouzi, F
    [J]. TETRAHEDRON LETTERS, 2003, 44 (28) : 5343 - 5345
  • [9] FULSTNER A, 2001, ORG LETT, V3, P417
  • [10] Group 5 and group 6 metal halides as very efficient catalysts for acylative cleavage of ethers
    Guo, QX
    Miyaji, T
    Hara, R
    Shen, BJ
    Takahashi, T
    [J]. TETRAHEDRON, 2002, 58 (36) : 7327 - 7334