Synthesis of tricyclic heterocycles via a tandem aryl alkylation/heck coupling sequence

被引:42
作者
Alberico, Dino [1 ]
Rudolph, Alena [1 ]
Lautens, Mark [1 ]
机构
[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
关键词
D O I
10.1021/jo0617868
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A norbornene-mediated palladium-catalyzed sequence is described in which two alkyl-aryl bonds and one alkenyl-aryl bond are formed in one pot with use of microwave irradiation. A variety of symmetrical and unsymmetrical oxygen-, nitrogen-, silicon-, and sulfur-containing tricyclic heterocycles were synthesized from a Heck acceptor and an aryl iodide containing two tethered alkyl halides. This approach was further applied to the synthesis of a tricyclic mescaline analogue.
引用
收藏
页码:775 / 781
页数:7
相关论文
共 55 条
  • [1] Synthesis of a tricyclic mescaline analogue by catalytic C-H bond activation
    Ahrendt, KA
    Bergman, RG
    Ellman, JA
    [J]. ORGANIC LETTERS, 2003, 5 (08) : 1301 - 1303
  • [2] Palladium-catalyzed sequential alkylation-alkenylation reactions: application towards the synthesis of polyfunctionalized fused aromatic rings
    Alberico, D
    Paquin, JF
    Lautens, M
    [J]. TETRAHEDRON, 2005, 61 (26) : 6283 - 6297
  • [3] Palladium-catalyzed alkylation-alkenylation reactions: Rapid access to tricyclic mescaline analogues
    Alberico, Dino
    Lautens, Mark
    [J]. SYNLETT, 2006, (18) : 2969 - 2972
  • [4] BROOK MA, 2000, SILICON ORGANIC ORGA, pCH16
  • [5] Catellani M, 2005, TOP ORGANOMETAL CHEM, V14, P21
  • [6] Catalytic multistep reactions via palladacycles
    Catellani, M
    [J]. SYNLETT, 2003, (03) : 298 - 313
  • [7] 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
  • [8] 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
  • [9] CATELLANI M, 2002, HDB ORGANOPALLADIUM, P1479
  • [10] Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position:: Effects on 5-HT2A/2C receptor affinity
    Chambers, JJ
    Kurrasch-Orbaugh, DM
    Nichols, DE
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (15) : 1997 - 1999