CuX2-mediated [4+2] benzannulation as a new synthetic tool for stereoselective construction of haloaromatic compounds

被引：51
作者：
Isogai, Yukie [1 ]
Menggenbateer [1 ]
Khan, F. Nawaz [1 ]
Asao, Naoki [1 ,2 ]
机构：
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Sendai, Miyagi 9808578, Japan
来源：
TETRAHEDRON | 2009年 / 65卷 / 46期
关键词：
C-H BONDS; THIN-FILM TRANSISTORS; ORGANIC SEMICONDUCTORS; SUBSTITUTED NAPHTHALENES; CATALYZED BENZANNULATION; TETRACENE DERIVATIVES; COUPLING REACTIONS; CONJUGATED ENYNES; HIGH-PERFORMANCE; LINEAR ACENES;
D O I：
10.1016/j.tet.2009.09.061
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The CuX2-mediated reaction of enynal units, including ortho-alkynylbenzaldehydes, with alkynes gives a variety of haloaromatic compounds stereoselectively in good to high yields. 2,2'-Binaphthyl skeletons are also readily prepared by the reaction of ortho-alkynylbenzaldehydes and diynes. The method was applied to the synthesis of poly-substituted tetracene derivatives (C) 2009 Elsevier Ltd. All rights reserved
引用
收藏
页码：9575 / 9582
页数：8
相关论文
共 84 条
  • [11] BAILUENGA J, 2007, ANGEW CHEM, V119, P1303
  • [12] BAILUENGA J, 2007, ANGEW CHEM INT EDIT, V46, P1281
  • [13] Regioselective synthesis of substituted naphthalenes:: A novel de novo approach based on a metal-free protocol for stepwise cycloaddition of o-alkynylbenzaldehyde derivatives with either alkynes or alkenes
    Barluenga, J
    Váquez-Villa, H
    Ballesteros, A
    González, JM
    [J]. ORGANIC LETTERS, 2003, 5 (22) : 4121 - 4123
  • [14] First total synthesis of naturally occurring (-)-nitidon and its enantiomer
    Bellina, F
    Carpita, A
    Mannocci, L
    Rossi, R
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (12) : 2610 - 2619
  • [15] Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: The brick and mortar of organic electronics
    Bendikov, M
    Wudl, F
    Perepichka, DF
    [J]. CHEMICAL REVIEWS, 2004, 104 (11) : 4891 - 4945
  • [16] Atroposelective synthesis of axially chiral biaryl compounds
    Bringmann, G
    Mortimer, AJP
    Keller, PA
    Gresser, MJ
    Garner, J
    Breuning, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) : 5384 - 5427
  • [17] Bringmann G., 2005, ANGEW CHEM INT EDIT, V117, P5518, DOI 10.1002/ange.200462661
  • [18] MARINE HALOPEROXIDASES
    BUTLER, A
    WALKER, JV
    [J]. CHEMICAL REVIEWS, 1993, 93 (05) : 1937 - 1944
  • [19] 5,6-bis(trimethylsilyl)benzo[c]furan:: an isolable versatile building block for linear polycyclic aromatic compounds
    Chan, SH
    Yick, CY
    Wong, HNC
    [J]. TETRAHEDRON, 2002, 58 (46) : 9413 - 9422
  • [20] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant
    Chen, Xiao
    Hao, Xue-Shi
    Goodhue, Charles E.
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6790 - 6791
123456789