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Synthesis 2008(23): 3755-3760  
DOI: 10.1055/s-0028-1083635
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Metal-Free Hydroarylation of Alkynes: A Very Convenient, Simple Procedure for Substituted Arylalkenes

Md. Ataur Rahman, Osamu Ogawa, Juzo Oyamada, Tsugio Kitamura*
Department of Chemistry and Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan
Fax: +81(952)288550; e-Mail: kitamura@cc.saga-u.ac.jp;
Further Information

Publication History

Received 4 July 2008
Publication Date:
06 November 2008 (online)

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Abstract

Hydroarylation of aryl-substituted alkynes with simple and substituted arenes was conducted in the presence of trifluoroacetic acid in dichloromethane without any metal catalysts or additives. Electron-rich arenes coupled with aryl-substituted alkynes to give 1,1-diarylalkenes in good to high yields.

Key words

hydroarylation - alkynes - arenes - trifluoroacetic acid

    References

  • 1a Carey FA. Sundberg RJ. Advanced Organic Chemistry   Part B, 4th ed.:  Kluwer Academic/Plenum Press; New York: 2001.  Chap. 11.
    Google Scholar
  • 1b Smith MB. March J. March’s Advanced Organic Chemistry   6th ed.:  Wiley-Interscience; New York: 2007.  Chap. 11.
    Google Scholar
  • 2a Fujiwara Y. Kitamura T. In Handbook of C-H Transformations   Dyker G. Wiley-VCH; Weinheim: 2005.  p.194 
    Google Scholar
  • 2b Jia C. Kitamura T. Fujiwara Y. Acc. Chem. Res.  2001,  34:  633 
    Google Scholar
  • 2c Oyamada J. Kitamura T. Chem. Lett.  2005,  34:  1430 
    Google Scholar
  • 2d Oyamada J. Kitamura T. Tetrahedron  2007,  63:  12754 
    Google Scholar
  • 2e Reetz MT. Sommer K. Eur. J. Org. Chem.  2003,  3485 
    Google Scholar
  • 2f Shi Z. He C. J. Org. Chem.  2004,  69:  3669 
    Google Scholar
  • 2g Nevado C. Echavarren AM. Synthesis  2005,  167 
    Google Scholar
  • 2h Nakao Y. Kanyiva KS. Hiyama T. J. Am. Chem. Soc.  2008,  130:  2448 
    Google Scholar
  • 2i Kakiuchi F. Chatani N. Adv. Synth. Catal.  2003,  345:  1077 
    Google Scholar
  • 2j Yoon MY. Kim JH. Choi DS. Shin US. Lee JY. Song CE. Adv. Synth. Catal.  2007,  349:  1725 
    Google Scholar
  • 2k Li R. Wang SR. Lu W. Org. Lett.  2007,  9:  2219 
    Google Scholar
  • 2l Biffis A. Tubaro C. Buscemi G. Basato M. Adv. Synth. Catal.  2008,  350:  189 
    Google Scholar
  • 3 Xing D. Guan B. Cai G. Fang Z. Yang L. Shi Z. Org. Lett.  2006,  8:  693 
    CrossrefPubMedGoogle Scholar
  • 4a Li K. Foresee LN. Tunge JA. J. Org. Chem.  2005,  70:  2881 
    Google Scholar
  • 4b Aoki S. Amamoto C. Oyamada J. Kitamura T. Tetrahedron  2005,  61:  9291 
    Google Scholar
  • 5 Carey FA. Sundberg RJ. Advanced Organic Chemistry   Part A, 4th ed.:  Kluwer Academic/Plenum Press; New York: 2000.  Chap. 10.
    Google Scholar
  • 6a Stang PJ. Anderson AG. Tetrahedron Lett.  1977,  18:  1485 
    Google Scholar
  • 6b Stang PJ. Anderson AG. J. Am. Chem. Soc.  1978,  100:  1520 
    Google Scholar
  • 6c Kitamura T. Kobayashi S. Taniguchi H. Rappoport Z. J. Org. Chem.  1982,  47:  5003 
    Google Scholar
  • 7 Jia C. Lu W. Oyamada J. Kitamura T. Matsuda K. Irie M. Fujiwara Y. J. Am. Chem. Soc.  2000,  122:  7252 
    CrossrefGoogle Scholar
  • 8a Barluenga J. Moriel P. Valdés C. Aznar F. Angew. Chem. Int. Ed.  2007,  46:  5587 
    Google Scholar
  • 8b Stavber S. Sotler-Pecan T. Zupan M. Bull. Chem. Soc. Jpn.  1996,  69:  169 
    Google Scholar
  • 8c Berthiol F. Doucet H. Santelli M. Eur. J. Org. Chem.  2003,  1091 
    Google Scholar
  • 10 Sun H. Hua R. Chen S. Yin Y. Adv. Synth. Catal.  2006,  348:  1919 
    CrossrefGoogle Scholar
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Identified by comparison with a commercial sample from Tokyo Chemical Industry Co.