PDF herunterladen
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;
Weitere Informationen

Publikationsverlauf

Received 1 December 2011
Publikationsdatum:
15. März 2012 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik

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 
    Suche in Google Scholar
  • 1b Doucet H. Hierso J.-C. Angew. Chem. Int. Ed.  2007,  46:  834 
    Suche in Google Scholar
  • 1c Saito S. Yamamoto Y. Chem. Rev.  2000,  100:  2901 
    Suche in Google Scholar
  • 1d Trost BM. Angew. Chem. Int. Ed.  1995,  34:  259 
    Suche 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 
    Suche in Google Scholar
  • 3b Chen X. Xue P. Sung HHY. Williams ID. Peruzzini M. Bianchini C. Jia G. Organometallics  2005,  24:  4330 
    Suche in Google Scholar
  • 3c Lee C.-C. Lin Y.-C. Liu Y.-H. Wang Y. Organometallics  2005,  24:  136 
    Suche in Google Scholar
  • 3d Komeyama K. Kawabata T. Takehira K. Takaki K. J. Org. Chem.  2005,  70:  7260 
    Suche 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 
    Suche in Google Scholar
  • 3h Nishiura M. Hou Z. Makatsuki Y. Yamaki T. Miyamoto T. J. Am. Chem. Soc.  2003,  125:  1184 
    Suche in Google Scholar
  • 3i Yang C. Nolan SP. J. Org. Chem.  2002,  67:  591 
    Suche in Google Scholar
  • 3j Rubina M. Gevorgyan V. J. Am. Chem. Soc.  2001,  123:  11107 
    Suche in Google Scholar
  • 3k Trost BM. Sorum MT. Chan C. Harms AE. Rühter G. J. Am. Chem. Soc.  1997,  119:  698 
    Suche in Google Scholar
  • 3l Trost BM. Chan C. Ruhter G. J. Am. Chem. Soc.  1987,  109:  3486 
    Suche 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 
    Suche in Google Scholar
  • 4c Stang PJ. Kitamura T. J. Am. Chem. Soc.  1987,  109:  7561 
    Suche 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 
    Suche in Google Scholar
  • 6b Chinchilla R. Nájera C. Chem. Rev.  2007,  107:  874 
    Suche in Google Scholar
  • 6c Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed.  2005,  44:  4442 
    Suche in Google Scholar
  • 6d Negishi E. Anastasia L. Chem. Rev.  2003,  103:  1979 
    Suche in Google Scholar
  • 6e Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 
    Suche in Google Scholar
  • 6f Siemsen P. Livingston RC. Diederich F. Angew. Chem. Int. Ed.  2000,  39:  2632 
    Suche in Google Scholar
  • 6g Martin RE. Diederich F. Angew. Chem. Int. Ed.  1999,  38:  1350 
    Suche in Google Scholar
  • 6h Grissom JW. Gunawardena GU. Klingberg D. Huang D. Tetrahedron  1996,  52:  6453 
    Suche in Google Scholar
  • 6i Nicolaou KC. Dai W.-M. Angew. Chem., Int. Ed. Engl.  1991,  30:  1387 
    Suche 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 
    Suche 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 
    Suche 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 
    Suche 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 
    Suche in Google Scholar
  • 7g Ma D. Liu F. Chem. Commun.  2004,  1934 
  • 7h Gujadhur RK. Bates CG. Venkataraman D. Org. Lett.  2001,  3:  4315 
    Suche in Google Scholar
  • 7i Okuro K. Furuune M. Enna M. Miura M. Nomura M. J. Org. Chem.  1993,  58:  4716 
    Suche 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 
    Suche 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 
    Suche in Google Scholar
  • 8e Okuro K. Furuune M. Enna M. Miura M. Nomura M. J. Org. Chem.  1993,  58:  4716 
    Suche in Google Scholar
  • 8f Okuro K. Furuune M. Miura M. Nomura M. Tetrahedron Lett.  1992,  33:  5363 
    Suche 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 
    Suche in Google Scholar
  • 9b Sakai N. Komatsu R. Uchida N. Ikeda R. Konakahara T. Org. Lett.  2010,  12:  1300 
    Suche in Google Scholar
  • 9c Hatakeyama T. Yoshimoto Y. Gabriel T. Nakamura M. Org. Lett.  2008,  10:  5341 
    Suche in Google Scholar
  • 9d Kang B. Kim D.-h. Do Y. Chang S. Org. Lett.  2003,  5:  3041 
    Suche in Google Scholar
  • 9e Shi J.-c. Zeng X. Negishi E.-i. Org. Lett.  2003,  5:  1825 
    Suche 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 
    Suche in Google Scholar