Palladium-catalyzed sequential alkylation-alkenylation reactions: application towards the synthesis of polyfunctionalized fused aromatic rings

被引:31
作者
Alberico, D [1 ]
Paquin, JF [1 ]
Lautens, M [1 ]
机构
[1] Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
palladium; catalysis; intramolecular heck reaction; norbornene; ortho functionalization; fused aromatic rings; catellani reaction;
D O I
10.1016/j.tet.2005.03.128
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of polyfunctionalized fused aromatic carbo- and heterocycles from aryl iodides and bromoenoates via a tandem palladium-catalyzed aromatic substitution intramolecular Heck sequence is reported. Using Pd(OAc)(2) and tri-2-furylphosphine (TFP) in the presence of norbornene and Cs2CO3 in CH3CN at 85 degrees C gave a variety of functionalized bi- and tricyclic fused aromatic rings in good yield. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6283 / 6297
页数:15
相关论文
共 47 条
  • [1] AMATORE C, 2000, ACCOUNTS CHEM RES, V100, P2963
  • [2] STERIC EFFECTS IN INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION OF C=C DOUBLE-BONDS TO CYCLOHEXENONES
    BECKER, D
    HADDAD, N
    [J]. TETRAHEDRON, 1993, 49 (04) : 947 - 964
  • [3] The heck reaction as a sharpening stone of palladium catalysis
    Beletskaya, IP
    Cheprakov, AV
    [J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
  • [4] BLOODWORTH AJ, 1990, J CHEM SOC P1, V11, P2951
  • [5] SYNTHESIS OF BIOLOGICALLY-ACTIVE UNSATURATED AMIDES
    BOHLMANN, F
    GANZER, M
    KRUGER, M
    NORDHOFF, E
    [J]. TETRAHEDRON, 1983, 39 (01) : 123 - 128
  • [6] BRAESE S, 2002, HDB ORGANOPALLADIUM, P1223
  • [7] Catalytic multistep reactions via palladacycles
    Catellani, M
    [J]. SYNLETT, 2003, (03) : 298 - 313
  • [8] Palladium-arene interactions in catalytic intermediates:: An experimental and theoretical investigation of the soft rearrangement between η1 and η2 coordination modes
    Catellani, M
    Mealli, C
    Motti, E
    Paoli, P
    Perez-Carreño, E
    Pregosin, PS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (16) : 4336 - 4346
  • [9] CATELLANI M, 1994, ANGEW CHEM INT EDIT, V33, P2421
  • [10] A complex catalytic cycle leading to a regioselective synthesis of o,o'-disubstituted vinylarenes
    Catellani, M
    Frignani, F
    Rangoni, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2): : 119 - 122