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
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
  • [41] Palladium-catalyzed fluorination of carbon-hydrogen bonds
    Hull, Kami L.
    Anani, Waseem Q.
    Sanford, Melanie S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) : 7134 - 7135
  • [42] Scope and selectivity in palladium-catalyzed directed C-H bond halogenation reactions
    Kalyani, Dipannita
    Dick, Allison R.
    Anani, Waseem Q.
    Sanford, Melanie S.
    [J]. TETRAHEDRON, 2006, 62 (49) : 11483 - 11498
  • [43] A simple catalytic method for the regioselective halogenation of arenes
    Kalyani, Dipannita
    Dick, Allison R.
    Anani, Waseem Q.
    Sanford, Melanie S.
    [J]. ORGANIC LETTERS, 2006, 8 (12) : 2523 - 2526
  • [44] Benzannulation
    Kotha, Sambasivarao
    Misra, Shilpi
    Halder, Somnath
    [J]. TETRAHEDRON, 2008, 64 (48) : 10775 - 10790
  • [45] THE INTERACTION OF SILICON WITH POSITIVELY CHARGED CARBON
    LAMBERT, JB
    [J]. TETRAHEDRON, 1990, 46 (08) : 2677 - 2689
  • [46] Iterative synthesis of acenes via homo-elongation
    Lin, Chih-Hsiu
    Lin, Ke-Han
    Pal, Bikash
    Tsou, Li-Der
    [J]. CHEMICAL COMMUNICATIONS, 2009, (07) : 803 - 805
  • [47] Synthesis of tetracene sulfoxide and tetracene sulfone via a cascade cyclization reaction
    Lin, Yi-Chun
    Lin, Chih-Hsiu
    [J]. ORGANIC LETTERS, 2007, 9 (11) : 2075 - 2078
  • [48] Littke A. F., 2002, ANGEW CHEM, V114, P4350
  • [49] Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO
  • [50] 2-U