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Synthesis 2008(19): 3047-3052  
DOI: 10.1055/s-2008-1067253
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Convenient One-Pot Synthesis of Bis[(E)-4-halostyryl]arene Derivatives

Wiesław Prukała, Mariusz Majchrzak, Krystian Posała, Bogdan Marciniec*
Department of Organometallic Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland
Fax: +48(61)8291508; e-Mail: marcinb@amu.edu.pl;
Further Information

Publication History

Received 17 March 2008
Publication Date:
04 September 2008 (online)

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Abstract

A new convenient synthetic protocol for the one-pot stereoselective synthesis of bis[(E)-4-bromo(or chloro)styryl]arene derivatives via the sequential reaction of silylative-coupling of 4-halostyrenes with vinylsilanes followed by palladium-catalyzed cross-coupling 4-halostyrylsilanes with diiodoarenes, is described. The reaction leads to symmetrical bis[(E)-4-halostyryl]arene derivatives obtained in a stereocontrolled manner with high efficiency.

Key words

vinylsilanes - transition metals catalysis - silylative cross-coupling

    References

  • 1a Special issue: Molecular Materials in Electronic and Optoelectronic Devices   Sheats JR. Barbara PF. Acc. Chem. Res. 1999.  32:  p.191-276  
  • 1b Videlot-Ackermann C. Ackermann J. Brisset H. Kawamura K. Yoshimoto N. Raynal P. El Kassmi A. Fages F. J. Am. Chem. Soc.  2005,  127:  16346 
    Search in Google Scholar
  • 1c Wilson JN. Bunz UHF. J. Am. Chem. Soc.  2005,  127:  4124 
    Search in Google Scholar
  • 1d Takeshi T, and Takaaki I. inventors; European Patent EP  1 843 211. 
  • 2 Meier H. Angew. Chem., Int. Ed. Engl.  1992,  31:  1399 
    CrossrefSearch in Google Scholar
  • 3a Weitzel HP. Müllen K. Makromol. Chem.  1990,  13:  563 
    Search in Google Scholar
  • 3b Suzuki M. Lim JC. Saegusa T. Macromolecules  1990,  23:  1574 
    Search in Google Scholar
  • 3c Scherf U. Mullen K. Synthesis  1992,  23 ; and literature cited therein
  • 3d Katayama H. Nagao M. Nishimura T. Matsui Y. Umeda K. Akamatsu K. Tsuruoka T. Nawafune H. Ozawa F. J. Am. Chem. Soc.  2005,  127:  4350 
    Search in Google Scholar
  • 3e Katayama H. Nagao M. Ozawa F. Ikegami M. Arai T. J. Org. Chem.  2006,  71:  2699 
    Search in Google Scholar
  • 3f Leclerc N. Sanaur S. Galmiche L. Mathevet F. Attias A.-J. Fave J.-L. Roussel J. Hapiot P. Lemaitre N. Geffroy B. Chem. Mater.  2005,  17:  502 
    Search in Google Scholar
  • 3g Egbe DAM. Tekin E. Berckner E. Pivrikas A. Sariciftci NS. Schubert US. Macromolecules  2007,  40:  7786 
    Search in Google Scholar
  • 4a Quintini M. inventors; US Patent 5 250  223. 
  • 4b Reinehr D, Sauter H, Kramer J, Weigmann R, Eckhardt C, and Meyer HR. inventors; European Patent EP  0900784. 
  • 4c Hhoaf GL, Ollis GW, Stockl RR, and Munjal RC. inventors; US Patent  0249764. 
  • 5a Frechet JM. Hawker CJ. Gitsov I. Leon JW. J. Macromol. Sci., Part A: Pure Appl. Chem.  1996,  A33:  1399 
    Search in Google Scholar
  • 5b Meier H. Lehmann M. Angew. Chem. Int. Ed.  1998,  37:  643 
    Search in Google Scholar
  • 5c Lo S.-C. Burn PL. Chem. Rev.  2007,  107:  1097 ; and literature cited therein
    Search in Google Scholar
  • 6a Friedrich K. Henning H.-G. Chem. Ber.  1959,  92:  2944 
    Search in Google Scholar
  • 6b Bontagy J. Thomas R. Chem. Rev.  1974,  74:  87 
    Search in Google Scholar
  • 6c Arient J. Collect. Czech. Chem. Commun.  1981,  46:  101 
    Search in Google Scholar
  • 6d Deb SK. Maddux TM. Yu L. J. Am. Chem. Soc.  1997,  119:  9079 
    Search in Google Scholar
  • 6e Pillow JNG. Halim M. Lupton JM. Burn PL. Samuel IDW. Macromolecules  1999,  32:  5985 
    Search in Google Scholar
  • 6f Segura JL. Gomez R. Martin N. Guldi DM. Org. Lett.  2001,  3:  2645 
    Search in Google Scholar
  • 6g Palsson L.-O. Beavington R. Frampton MJ. Lupon JM. Magennis SW. Markham JPJ. Pillow JNG. Burn PL. Samuel IDW. Macromolecules  2002,  35:  7891 
    Search in Google Scholar
  • 6h Cano-Marin AR. Diez-Barra E. Rodriguez-Lopez J. Tetrahedron  2005,  61:  395 
    Search in Google Scholar
  • 7a Sengupta S. Sadhukhan SK. Singh RS. Pal N. Tetrahedron Lett.  2002,  43:  1117 
    Search in Google Scholar
  • 7b Itami K. Tonogaki K. Nokami T. Ohashi Y. Yoshida J. Angew. Chem. Int. Ed.  2006,  45:  2404 
    Search in Google Scholar
  • 8a Katayama H. Nagao M. Nishimura T. Matsui Y. Fukuse Y. Wakioka M. Ozawa F. Macromolecules  2006,  39:  2039 
    Search in Google Scholar
  • 8b Katayama H. Nagao M. Ozawa F. Ikegami M. Arai T. J. Org. Chem.  2006,  71:  2699 
    Search in Google Scholar
  • 9a Marciniec B. Pietraszuk C. Handbook of Metathesis   Vol. 2:  Grubbs R. Wiley-VCH; Weinheim: 2003. 
    Search in Google Scholar
  • 9b Marciniec B. Zaidlewicz M. Pietraszuk C. Kownacki I. In Comprehensive Organic Functional Group Transformations II   Vol. 2:  Katritzky AR. Taylor RJK. Elsevier Science; Amsterdam: 2005.  p.941-1024  
    Search in Google Scholar
  • 9c Marciniec B. Coord. Chem. Rev.  2005,  249:  2374 
    Search in Google Scholar
  • 9d Marciniec B. Acc. Chem. Res.  2007,  40:  943 
    Search in Google Scholar
  • 10a Hiyama T. In Handbook of Organopalladium Chemistry for Organic Synthesis   Vol. 1:  Negishi E. Wiley-Interscience; New York: 2002.  p.285 
    Search in Google Scholar
  • 10b Hiyama T. In Metal-Catalyzed Cross-Coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998. 
  • 10c Prukaa W. Majchrzak M. Pietraszuk C. Marciniec B. J. Mol. Catal. A: Chem.  2006,  254:  58 
    Search in Google Scholar
  • 10d Prukaa W. Pawluć P. Posaa K. Marciniec B. Synlett  2008,  41 
  • 11a Levison JJ. Robinson SD. J. Chem. Soc. A  1970,  2947 
  • 11b Ahmad N. Levison JJ. Robinson SD. Uttley MF. Inorg. Synth.  1974,  15:  45 
    Search in Google Scholar
  • 12 Ukai T. Kawazura H. Ishii Y. J. Organomet. Chem.  1974,  65:  253 
    CrossrefSearch in Google Scholar