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Synlett 2011(6): 741-744  
DOI: 10.1055/s-0030-1259712
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© Georg Thieme Verlag Stuttgart ˙ New York

Metal-Catalyzed Cascade Reactions of Ethynyl-Substituted Naphthalenes: Synthesis of Polycyclic Arenes

Tsun-Cheng Wu, Yao-Ting Wu*
Department of Chemistry, National Cheng Kung University, No. 1 Ta-Hsueh Rd., 70101 Tainan, Taiwan, ROC
Fax: +886(6)2740552; e-Mail: ytwuchem@mail.ncku.edu.tw;
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Publication History

Received 8 November 2010
Publication Date:
08 March 2011 (online)

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Abstract

Palladium-catalyzed cycloaddition reactions of 1,8-diethynylnaphthalene derivatives with o-diiodoarenes take place to generate the corresponding benzo[k]fluoranthene-based linear acenes in moderate to good yields. In addition, 1-ethynyl-8-iodo­naphthalenes undergo palladium-catalyzed cyclodimerizations to produce zethrenes. Finally, in the presence of a catalytic system comprised of [NiBr2(dppe)/Zn], 1-ethynyl-8-iodonaphthalenes reacts with nitriles and 2-butyne to form the respective pyrroloarenes and pyrene.

Key words

arenes - cross-coupling - cycloadditon - nickel - palladium - polycycles

    References and Notes

  • 1 Harvey RG. Polycyclic Aromatic Hydrocarbons   Wiley-VCH; New York: 1997. 
    Google Scholar
  • Selected reviews for organic materials based on PA:
  • 2a Collings PJ. Hird M. Introduction to Liquid Crystals: Chemistry and Physics   Taylor and Francis; London: 1997. 
    Google Scholar
  • 2b Organic Light Emitting Devices: Synthesis, Properties and Applications   Müllen K. Scherf U. Wiley-VCH; Weinheim: 2005. 
    Google Scholar
  • 2c Introduction to Organic Electronic and Optoelectronic Materials and Devices   Sun S.-S. Dalton LR. CRC; New York: 2008. 
    Google Scholar
  • 2d Hatton RA. Miller AJ. Silva SRP. J. Mater. Chem.  2008,  18:  1183 
    Google Scholar
  • 2e Wu J. Curr. Org. Chem.  2007,  11:  1220 
    Google Scholar
  • 2f Imahori H. Umeyama T. Ito S. Acc. Chem. Res.  2009,  42:  1809 
    Google Scholar
  • 3a Huang W. Zhou X. Kanno K.-i. Takahashi T. Org. Lett.  2004,  6:  2429 
    Google Scholar
  • 3b Dyker G. J. Org. Chem.  1993,  58:  234 
    Google Scholar
  • 3c Kawasaki S. Satoh T. Miura M. Nomura M.
    J. Org. Chem.  2003,  68:  6836 
    Google Scholar
  • 3d Larock RC. Doty MJ. Tian Q. Zenner JM. J. Org. Chem.  1997,  62:  7536 
    Google Scholar
  • 3e Hsieh JC. Cheng CH. Chem. Commun.  2008,  2992 
    Google Scholar
  • 3f Levi ZU. Tilley TD. J. Am. Chem. Soc.  2009,  131:  2796 
    Google Scholar
  • 3g Kawase T. Konishi A. Hirao Y. Matsumoto K. Kurata H. Kubo T. Chem. Eur. J.  2009,  15:  2653 
    Google Scholar
  • Reviews:
  • 3h Larock RC. In Acetylene Chemistry: Chemistry, Biology, and Material Science   Stang PJ. Tykwinski RR. Diederich F. Wiley-VCH; Weinheim: 2005.  p.51 
    Google Scholar
  • 3i Tsuji J. Palladium Reagents and Catalysts   2nd ed.:  Wiley; Chichester: 2004.  p.231 
    Google Scholar
  • 4a Bergmann E. Nature (London)  1948,  161:  889 
    Google Scholar
  • 4b Bergmann E. J. Am. Chem. Soc.  1952,  74:  1075 
    Google Scholar
  • 4c Allen CF. VanAllan HJA. J. Org. Chem.  1952,  17:  845 
    Google Scholar
  • 5 Kung Y.-H. Cheng Y.-S. Tai C.-C. Liu W.-S. Shin C.-C. Ma C.-C. Tsai Y.-C. Wu T.-C. Kuo M.-Y. Wu Y.-T. Chem. Eur. J.  2010,  16:  5909 
    CrossrefPubMedGoogle Scholar
  • 6A recent review for zethrene:
  • 6 Umeda R. Hibi D. Miki K. Tobe Y. Pure Appl. Chem.  2010,  82:  871 
    CrossrefGoogle Scholar
  • 7a Mitchell RH. Sondheimer F. J. Am. Chem. Soc.  1968,  90:  530 
    Google Scholar
  • 7b Meinwald J. Young JW. J. Am. Chem. Soc.  1971,  93:  725 
    Google Scholar
  • 7c Staab HA. Nissen A. Ipaktschi J. Angew. Chem., Int. Ed. Engl.  1968,  7:  226 
    Google Scholar
  • 7d Umeda R. Hibi D. Miki K. Tobe Y. Org. Lett.  2009,  11:  4104 
    Google Scholar
  • 7e Sun Z. Huang K.-W. Wu J. Org. Lett.  2010,  12:  4690 
    Google Scholar
  • 8 Wu T.-C. Chen C.-H. Hibi D. Shimizu A. Tobe Y. Wu Y.-T. Angew. Chem. Int. Ed.  2010,  49:  7059 
    CrossrefGoogle Scholar
  • 9a Clar E. The Aromatic Sextet   John Wiley and Sons; London: 1972. 
    Google Scholar
  • 9b Clar E. Polycyclic Hydrocarbons   Vol. 1 and 2:  Academic; London: 1964. 
    Google Scholar
  • 10a Frank NL. Baldridge KK. Siegel JS. J. Am. Chem. Soc.  1995,  117:  2102 
    Google Scholar
  • 10b Bürgi H.-B. Baldridge KK. Hardcastle K. Frank NL. Gantzel P. Siegel JS. Ziller J. Angew. Chem., Int. Ed. Engl.  1995,  34:  1454 
    Google Scholar
  • 11 Wu T.-C. Tai C.-C. Tiao H.-C. Kuo M.-Y. Wu Y.-T. Chem. Eur. J.  2011,  17:  1930 
    CrossrefGoogle Scholar
12

The structure of 13 has been confirmed by X-ray structural analysis (Wu, T.-C.; Wu, Y.-T. unpublished results).