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

被引:50
|
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 50 条
  • [31] A NEW CYCLIZATION REACTIONS CASCADE-ENE TYPE, [2+2+2], [4+2] - STEREOSELECTIVE FORMATION OF 6 CARBON-CARBON BONDS AND 4 RINGS IN A ONE-POT SEQUENCE
    CRUCIANI, P
    AUBERT, C
    MALACRIA, M
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09): : 2664 - 2665
  • [32] Dramatic acceleration of the Pd-catalyzed [4+2] benzannulation reaction of enynes and diynes in the presence of Lewis acids and bases: Expanded scope and new mechanistic insights
    Rubina, M
    Conley, M
    Gevorgyan, V
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (17) : 5818 - 5827
  • [33] Dramatic acceleration of the Pd-catalyzed [4+2] benzannulation reaction of enynes and diynes in the presence of Lewis acids and bases: Expanded scope and new mechanistic insights
    Rubina, Marina
    Conley, Matthew
    Gevorgyan, Vladimir
    Journal of the American Chemical Society, 2006, 128 (17): : 5818 - 5827
  • [34] [4+2] Cycloaddition Mediated Stereoselective Synthesis of Tetrahydro-1H-Isobenzofuro Chromene Dione Derivatives: Antibacterial Evaluation and Molecular Docking Investigation
    Parida, Sonali Priyadarshini
    Mohapatra, Suhasini
    Nayak, Sabita
    Mohapatra, Seetaram
    Panda, Jasmine
    Sahoo, Chita Ranjan
    CHEMISTRYSELECT, 2024, 9 (35):
  • [35] Intramolecular [4+2] cycloaddition of conjugated enynes with arynes: An efficient strategy for the construction of highly condensed polycyclic aromatic and heteroaromatic compounds.
    Hayes, ME
    Danheiser, RL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U175 - U175
  • [36] Synthesis of vinca alkaloids and related compounds.: Part 109.: An intramolecular [4+2] cycloaddition mediated biomimetic synthesis of (+/-)-iboxyphylline
    Toth, Florian
    Kalaus, Gyoergy
    Pipa, Gergely
    Greiner, Istvan
    Szollosy, Aron
    Rill, Attila
    Gomory, Agnes
    Hazai, Laszlo
    Szantay, Csaba
    HETEROCYCLES, 2008, 75 (01) : 65 - 76
  • [37] Green and Rapid Access to Benzocoumarins via Direct Benzene Construction through Base-Mediated Formal [4+2] Reaction and Air Oxidation
    Mou, Chengli
    Zhu, Tingshun
    Zheng, Pengcheng
    Yang, Song
    Song, Bao-An
    Chi, Yonggui Robin
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (05) : 707 - 712
  • [38] GaCl3-Mediated Cascade [2+4]-Cycloaddition/[4+2]-Annulation of Donor-Acceptor Cyclopropanes with Conjugated Dienes: Strategy for the Construction of Benzobicyclo[3.3.1]nonane Skeleton
    Belaya, Maria A.
    Knyazev, Daniil A.
    Borisov, Denis D.
    Novikov, Roman A.
    Tomilov, Yury, V
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (12): : 8089 - 8100
  • [39] New synthetic technology for the rapid construction of novel heterocycles - Part 2. The reaction of IBX with anilides and related compounds
    Nicolaou, KC
    Zhong, YL
    Baran, PS
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (03) : 625 - +
  • [40] New synthetic technology for the rapid construction of novel heterocycles - Part 2. The reaction of IBX with anilides and related compounds
    Nicolaou, K.C.
    Zhong, Yong-Li
    Baran, Phil S.
    2000, Wiley-VCH Verlag (39):