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Synlett 2012(6): 930-934  
DOI: 10.1055/s-0031-1290502
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Coupling of Alkynes with Alkenyl Halides

Yun-Yung Lin, Yu-Jen Wang, Jun-Hao Cheng, Chin-Fa Lee*
Department of Chemistry, National Chung Hsing University, Taichung, Taiwan 402, Republic of China
Fax: +886(4)22862547; e-Mail: cfalee@dragon.nchu.edu.tw;
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Publication History

Received 1 December 2011
Publication Date:
15 March 2012 (online)

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Abstract

The synthesis of enynes from the coupling of terminal alkynes with alkenyl iodides and bromides is described. This system employs 1.0-5.0 mol% of CuI(Xantphos) as a catalyst. A variety of alkenyl iodides and bromides are coupled smoothly with terminal alkynes, affording enynes in good to excellent yields.

Key words

copper - cross-coupling - terminal alkyne - alkenyl halide - enyne

    References

  • For reviews, see:
  • 1a Chinchilla R. Nájera C. Chem. Rev.  2007,  107:  874 
    Search in Google Scholar
  • 1b Doucet H. Hierso J.-C. Angew. Chem. Int. Ed.  2007,  46:  834 
    Search in Google Scholar
  • 1c Saito S. Yamamoto Y. Chem. Rev.  2000,  100:  2901 
    Search in Google Scholar
  • 1d Trost BM. Angew. Chem. Int. Ed.  1995,  34:  259 
    Search in Google Scholar
  • 2 Nicolaou KC. Smith AL. In Modern Acetylene Chemistry   Stang PJ. Diederich F. VCH; Weinheim: 1995. 
  • For examples, see:
  • 3a Bassetti M. Pasquini C. Raneri A. Rosato D. J. Org. Chem.  2007,  72:  4558 
    Search in Google Scholar
  • 3b Chen X. Xue P. Sung HHY. Williams ID. Peruzzini M. Bianchini C. Jia G. Organometallics  2005,  24:  4330 
    Search in Google Scholar
  • 3c Lee C.-C. Lin Y.-C. Liu Y.-H. Wang Y. Organometallics  2005,  24:  136 
    Search in Google Scholar
  • 3d Komeyama K. Kawabata T. Takehira K. Takaki K. J. Org. Chem.  2005,  70:  7260 
    Search in Google Scholar
  • 3e Katayama H. Yari H. Tanaka M. Ozawa F. Chem. Commun.  2005,  4336 
  • 3f Ogoshi S. Ueta M. Oka M. Kurosawa H. Chem. Commun.  2004,  2732 
  • 3g Katayama H. Nakayama M. Nakano T. Wada C. Akamatsu K. Ozawa F. Macromolecules  2004,  37:  13 
    Search in Google Scholar
  • 3h Nishiura M. Hou Z. Makatsuki Y. Yamaki T. Miyamoto T. J. Am. Chem. Soc.  2003,  125:  1184 
    Search in Google Scholar
  • 3i Yang C. Nolan SP. J. Org. Chem.  2002,  67:  591 
    Search in Google Scholar
  • 3j Rubina M. Gevorgyan V. J. Am. Chem. Soc.  2001,  123:  11107 
    Search in Google Scholar
  • 3k Trost BM. Sorum MT. Chan C. Harms AE. Rühter G. J. Am. Chem. Soc.  1997,  119:  698 
    Search in Google Scholar
  • 3l Trost BM. Chan C. Ruhter G. J. Am. Chem. Soc.  1987,  109:  3486 
    Search in Google Scholar
  • 4a Hoshi M. Nakayabu HH. Shirakawa K. Synthesis  2005,  1991 
  • 4b Silveira CC. Braga AL. Vieira AS. Zeni G. J. Org. Chem.  2003,  68:  662 
    Search in Google Scholar
  • 4c Stang PJ. Kitamura T. J. Am. Chem. Soc.  1987,  109:  7561 
    Search in Google Scholar
  • 5a Sonogashira K. In Handbook of Organopalladium Chemistry for Organic Synthesis   Negishi E. Wiley; New York: 2002.  p.493-529  
  • 5b Negishi E. Xu C. In Handbook of Organopalladium Chemistry for Organic Synthesis   Negishi E. Wiley; New York: 2002.  p.531-549  
  • For reviews, see:
  • 6a Heravi MM. Sadjadi S. Tetrahedron  2009,  65:  7761 
    Search in Google Scholar
  • 6b Chinchilla R. Nájera C. Chem. Rev.  2007,  107:  874 
    Search in Google Scholar
  • 6c Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed.  2005,  44:  4442 
    Search in Google Scholar
  • 6d Negishi E. Anastasia L. Chem. Rev.  2003,  103:  1979 
    Search in Google Scholar
  • 6e Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 
    Search in Google Scholar
  • 6f Siemsen P. Livingston RC. Diederich F. Angew. Chem. Int. Ed.  2000,  39:  2632 
    Search in Google Scholar
  • 6g Martin RE. Diederich F. Angew. Chem. Int. Ed.  1999,  38:  1350 
    Search in Google Scholar
  • 6h Grissom JW. Gunawardena GU. Klingberg D. Huang D. Tetrahedron  1996,  52:  6453 
    Search in Google Scholar
  • 6i Nicolaou KC. Dai W.-M. Angew. Chem., Int. Ed. Engl.  1991,  30:  1387 
    Search in Google Scholar
  • For selected examples, see:
  • 7a Lin C.-H. Wang Y.-J. Lee C.-F. Eur. J. Org. Chem.  2010,  4368 
  • 7b Monnier F. Turtaut F. Duroure L. Taillefer M. Org. Lett.  2008,  10:  3203 
    Search in Google Scholar
  • 7c Li J.-H. Li J.-L. Wang D.-P. Pi S.-F. Xie Y.-X. Zhang M.-B. Hu X.-C. J. Org. Chem.  2007,  72:  2053 
    Search in Google Scholar
  • 7d Xie Y.-X. Deng C.-L. Pi S.-F. Li J.-H. Yin D.-L. Chin. J. Chem.  2006,  24:  1290 
    Search in Google Scholar
  • 7e Saejueng P. Bates CG. Venkataraman D. Synthesis  2005,  1706 
  • 7f Wang YF. Deng W. Liu L. Guo QX. Chin. Chem. Lett.  2005,  16:  1197 
    Search in Google Scholar
  • 7g Ma D. Liu F. Chem. Commun.  2004,  1934 
  • 7h Gujadhur RK. Bates CG. Venkataraman D. Org. Lett.  2001,  3:  4315 
    Search in Google Scholar
  • 7i Okuro K. Furuune M. Enna M. Miura M. Nomura M. J. Org. Chem.  1993,  58:  4716 
    Search in Google Scholar
  • 8a Liu Y. Yang J. Bao W. Eur. J. Org. Chem.  2009,  5317 
  • 8b Xie X. Xu XB. Li HF. Xu XL. Yang JY. Li YZ. Adv. Synth. Catal.  2009,  351:  1263 
    Search in Google Scholar
  • 8c Wu M. Mao J. Guo J. Ji S. Eur. J. Org. Chem.  2008,  4050 
  • 8d Bates CG. Saejueng P. Venkataraman D. Org. Lett.  2004,  6:  1441 
    Search in Google Scholar
  • 8e Okuro K. Furuune M. Enna M. Miura M. Nomura M. J. Org. Chem.  1993,  58:  4716 
    Search in Google Scholar
  • 8f Okuro K. Furuune M. Miura M. Nomura M. Tetrahedron Lett.  1992,  33:  5363 
    Search in Google Scholar
  • Other methods for preparing enynes, see:
  • 9a Zhou L. Ye F. Ma J. Zhang Y. Wang J. Angew. Chem. Int. Ed.  2011,  50:  3510 
    Search in Google Scholar
  • 9b Sakai N. Komatsu R. Uchida N. Ikeda R. Konakahara T. Org. Lett.  2010,  12:  1300 
    Search in Google Scholar
  • 9c Hatakeyama T. Yoshimoto Y. Gabriel T. Nakamura M. Org. Lett.  2008,  10:  5341 
    Search in Google Scholar
  • 9d Kang B. Kim D.-h. Do Y. Chang S. Org. Lett.  2003,  5:  3041 
    Search in Google Scholar
  • 9e Shi J.-c. Zeng X. Negishi E.-i. Org. Lett.  2003,  5:  1825 
    Search in Google Scholar
  • 10 Huang J. Chan J. Chen Y. Borths CJ. Baucom KD. Larsen RD. Faul MM. J. Am. Chem. Soc.  2010,  132:  3674 
    Search in Google Scholar