Catalytic Friedel-Crafts acylation of benzene, chlorobenzene, and fluorobenzene using a novel catalyst system, hafnium triflate and trifluoromethanesulfonic acid

被引:92
作者
Kobayashi, S [1 ]
Iwamoto, S [1 ]
机构
[1] Sci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 162, Japan
关键词
D O I
10.1016/S0040-4039(98)00881-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytic Friedel-Crafts acylation of benzene and unactivated benzenes such as chlorobenzene and fluorobenzene has been successfully carried out using hafnium (IV) triflate and trifluoromethanesulfonic acid as catalysts. Both aromatic and aliphatic carboxylic acid chlorides reacted smoothly under the conditions to afford the corresponding aromatic ketones in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4697 / 4700
页数:4
相关论文
共 35 条
  • [1] 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
  • [2] ON THE TRANSITION-STATE FOR CLAYZIC-CATALYZED FRIEDEL-CRAFTS REACTIONS UPON ANISOLE
    CORNELIS, A
    LASZLO, P
    WANG, S
    [J]. TETRAHEDRON LETTERS, 1993, 34 (24) : 3849 - 3852
  • [3] 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
  • [4] The first unequivocal evidence of the reacting electrophile in aromatic acylation reactions
    Effenberger, F
    Eberhard, JK
    Maier, AH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (50) : 12572 - 12579
  • [5] CATALYTIC FRIEDEL-CRAFTS ACYLATION OF AROMATIC-COMPOUNDS
    EFFENBERGER, F
    EPPLE, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (04) : 300 - +
  • [6] INTRAMOLECULAR FRIEDEL-CRAFTS ACYLATION OF N-PHTHALOYL-SUBSTITUTED ARYLALANYL AND HOMOPHENYLALANYL CHLORIDES
    EFFENBERGER, F
    STEEGMULLER, D
    NULL, V
    ZIEGLER, T
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (01): : 125 - 130
  • [7] FERRIC CHLORIDE-CATALYZED ACYLATION OF AROMATIC-COMPOUNDS WITH N-PHTHALOYL-ALPHA-AMINO ACYL CHLORIDES WITHOUT RACEMIZATION
    EFFENBERGER, F
    STEEGMULLER, D
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (01): : 117 - 123
  • [8] Effenberger F., 1972, Angew. Chem. Int. Ed, V11, P299, DOI [10.1002/anie.197202991, DOI 10.1002/ANIE.197202991]
  • [9] CATALYTIC FRIEDEL-CRAFTS ACYLATION REACTIONS USING HAFNIUM TRIFLATE AS A CATALYST IN LITHIUM PERCHLORATE-NITROMETHANE
    HACHIYA, I
    MORIWAKI, M
    KOBAYASHI, S
    [J]. TETRAHEDRON LETTERS, 1995, 36 (03) : 409 - 412
  • [10] HAFNIUM(IV) TRIFLUOROMETHANESULFONATE, AN EFFICIENT CATALYST FOR THE FRIEDEL-CRAFTS ACYLATION AND ALKYLATION REACTIONS
    HACHIYA, I
    MORIWAKI, M
    KOBAYASHI, S
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (07) : 2053 - 2060