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Synlett 2009(3): 441-446  
DOI: 10.1055/s-0028-1087553
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper(I) Halide Catalyzed Three-Component Coupling Reaction of Aldehyde, Pyrrolidine and Stannyl- and Silylacetylene

Adam Shih-Yuan Lee*, Ge-An Chen, Yu-Ting Chang, Shu-Fang Chu
Department of Chemistry, Tamkang University, Tamsui, Taipei 25137, Taiwan
Fax: +886(2)26223830; e-Mail: adamlee@mail.tku.edu.tw;
Further Information

Publication History

Received 23 September 2008
Publication Date:
21 January 2009 (online)

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Abstract

An efficient three-component coupling reaction of aldehyde, pyrrolidine and tributylstannylacetylene or triphenylsilylacety-lene to generate propargylamines has been developed by using copper(I) halides as promoters.

Key words

three-component coupling reaction - propargylamine - tributylstannylacetylene - triphenylsilylacetylene

    References and Notes

  • 1a Jiang B. Si Y.-G. Angew. Chem. Int. Ed.  2004,  43:  216 
    Google Scholar
  • 1b Wright JL. Gregory TF. Kesten SR. Boxer PA. Serpa KA. Meltzer LT. Wise LD. J. Med. Chem.  2000,  43:  3408 
    Google Scholar
  • 1c Zablocki JA. Miyano M. Garland B. Pireh D. Schretzman L. Rao SN. Lindmark RJ. Panzer-Knodle S. Nicholson N. Taite B. Salyers A. King L. Feigen L. J. Med. Chem.  1993,  36:  1811 
    Google Scholar
  • 1d Nilsson B. Vargas HM. Ringdahl B. Hacksell U.
    J. Med. Chem.  1992,  35:  285 
    Google Scholar
  • 1e Yu PH. Davis BA. Boulton AA. J. Med. Chem.  1992,  35:  3713 
    Google Scholar
  • 1f Zablocki JA. Miyano M. Rao SN. Panzer-Knodle S. Nicholson N. Feigen L. J. Med. Chem.  1992,  35:  4914 
    Google Scholar
  • 1g Moon MW. Chidester CG. Heier RF. Morris JK. Collins RJ. Russell RR. Francis JW. Sage GP. Sethy VH. J. Med. Chem.  1991,  34:  2314 
    Google Scholar
  • 2a Hay AS. J. Org. Chem.  1962,  27:  3320 
    Google Scholar
  • 2b Rubin Y. Lin SS. Knobler CB. Anthony J. Boldi AM. Diederich F. J. Am. Chem. Soc.  1991,  113:  6943 
    Google Scholar
  • 2c Gibtner T. Hampel F. Gisselbrecht J.-P. Hirsch A. Chem. Eur. J.  2002,  8:  408 
    Google Scholar
  • 3a Likhar PR. Roy S. Roy M. Subhas MS. Kantam ML. De R L. Synlett  2007,  2301 
    Google Scholar
  • 3b Sakaguchi S. Mizuta T. Ishii Y. Org. Lett.  2006,  8:  2459 
    Google Scholar
  • 3c Park SB. Alper H. Chem. Commun.  2005,  1315 
    Google Scholar
  • 3d Sakaguchi S. Mizuta T. Furuwan M. Kubo T. Ishii Y. Chem. Commun.  2004,  1638 
    Google Scholar
  • 3e Choudary BM. Sridhar C. Kantam ML. Sreedhar B. Tetrahedron Lett.  2004,  45:  7319 
    Google Scholar
  • 3f Fischer C. Carreira EM. Synthesis  2004,  1497 
    Google Scholar
  • 3g Sakaguchi S. Kubo T. Ishii Y. Angew. Chem. Int. Ed.  2001,  40:  2534 
    Google Scholar
  • 4a Mitchell TN. Synthesis  1992,  803 
    Google Scholar
  • 4b Pereye M. Quintard J.-P. Rahm A. Tin in Organic Synthesis   Butterworths; London: 1987. 
    Google Scholar
  • 4c Desponds O. Schlosser M. J. Organomet. Chem.  1991,  409:  93 
    Google Scholar
  • 4d Li G. Zhao G. Org. Lett.  2006,  8:  633 
    Google Scholar
  • 6a Wei C. Li Z. Li C.-J. Org. Lett.  2003,  5:  4473 
    Google Scholar
  • 6b Wei C. Li C.-J. J. Am. Chem. Soc.  2003,  125:  9584 
    Google Scholar
  • 6c Li C.-J. Wei C. Chem. Commun.  2002,  268 
    Google Scholar
  • 6d Gommermann N. Knochel P. Chem. Eur. J.  2006,  12:  4380 
    Google Scholar
  • 7a Colvin EW. Silicon Reagents in Organic Synthesis   Academic Press; New York: 1988. 
    Google Scholar
  • 7b Knopfel TF. Aschwanden P. Inchikawa T. Watanabe T. Carreira EM. Angew. Chem. Int. Ed.  2004,  43:  5971 
    Google Scholar
  • 7c Gommermann N. Knochel P. Synlett  2005,  2799 
    Google Scholar
  • 8a Shi L. Tu Y.-Q. Wang M. Zhang F.-M. Fan C.-A. Org. Lett.  2004,  6:  1001 
    Google Scholar
  • 8b Wei CM. Li C.-J. J. Am. Chem. Soc.  2002,  124:  5638 
    Google Scholar
  • 8c Larhed M. Larhed M. Moberg C. Hallberg A. Acc. Chem. Res.  2002,  35:  717 
    Google Scholar
5

Dialkyne 1: ¹H NMR (CDCl3): δ = 1.75-1.84 (m, 8 H), 2.62-2.66 (m, 8 H), 4.78 (s, 2 H), 7.25-7.38 (m, 6 H), 7.51-7.55 (m, 4 H). ¹³C NMR (CDCl3): δ = 23.4, 50.0, 59.1, 71.0, 76.3, 127.7, 128.0, 128.2, 138.5. MS: m/z = 368(56) [M], 298(base), 297(48), 228(46), 175(22), 105(60).