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Synthesis 2008(24): 3988-3994  
DOI: 10.1055/s-0028-1083251
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Cross-Coupling Reactions of 1,2-Diiodoalkenes with Terminal Alkynes: Selective Synthesis of Unsymmetrical Buta-1,3-diynes and 2-Ethynylbenzofurans

Yun Lianga, Li-Ming Taoa,b, Yue-Hua Zhanga, Jin-Heng Li*a
a Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China
Fax: +86(731)8872101; e-Mail: jhli@hunnu.edu.cn;
b Department of Chemistry and Life Science, Xiangnan University, Chenzhou 423000, P. R. of China
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Publication History

Received 30 June 2008
Publication Date:
01 December 2008 (online)

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Abstract

(E)-1,2-Diiodoalkenes were found to be effective building blocks for the preparation of unsymmetrical buta-1,3-diynes and 2-ethynylbenzofurans. In the presence of palladium(II) acetate and copper(I) iodide, unsymmetrical buta-1,3-diynes were selectively obtained in moderate to good yields. Moreover, 2-ethynylbenzofurans were obtained in one pot from the reaction of 2-ethynylphenol with (E)-1,2-diiodoalkenes, palladium(II) acetate, and copper(I) iodide by simple heating.

Key words

palladium(II) acetate - copper(I) iodide - (E)-1,2-diiodoalkene - terminal alkyne - buta-1,3-diyne - 2-ethynylbenzofuran

    References

  • For selected reviews, see:
  • 1a Bohlmann F. In Chemistry of Acetylenes   Viehe HG. Dekker; New York: 1969.  Chap. 14. p.977-986  
    Google Scholar
  • 1b Eglinton G. McCrae W. Adv. Org. Chem.  1963,  4:  225 
    Google Scholar
  • 1c Bu’Lock JD. Prog. Org. Chem.  1964,  6:  86 
    Google Scholar
  • 1d Bohlmann F. Burkhardt H. Zdero C. Naturally Occurring Acetylenes   Academic Press; New York: 1973. 
    Google Scholar
  • 1e Towers HN. Page JE. Hudson JB. Curr. Org. Chem.  1997,  1:  395 
    Google Scholar
  • 1f Christensen LP. Phytochemistry  1992,  31:  7 ; and references cited therein
    Google Scholar
  • 1g Siemsen P. Livingston RC. Diederich F. Angew. Chem. Int. Ed.  2000,  39:  2633 
    Google Scholar
  • 1h Shun ALKS. Tykwinski RR. Angew. Chem. Int. Ed.  2006,  45:  1034 
    Google Scholar
  • 2a Glaser C. Ber. Dtsch. Chem. Ges.  1869,  2:  422 
    Google Scholar
  • 2b Glaser C. Ann. Chem. Pharm.  1870,  154:  137 
    Google Scholar
  • 2c Hay AS. J. Org. Chem.  1962,  27:  3320 
    Google Scholar
  • For selected examples, see:
  • 3a Niedballa U. Houben-Weyl   4th ed., Vol. 5/2a:  Georg Thieme Verlag; Stuttgart: 1977.  p.925-937  
    Google Scholar
  • 3b Boldi AM. Anthony J. Gramlich V. Knobler CB. Boudon C. Gisselbrecht JP. Gross M. Diederich F. Helv. Chim. Acta  1995,  78:  779 
    Google Scholar
  • 4a Chodkiewicz W. Cadiot P. C. R. Hebd. Seances Acad. Sci.  1955,  241:  1055 
    Google Scholar
  • 4b Chodkiewicz W. Ann. Chim. (Paris)  1957,  2:  819 
    Google Scholar
  • For representative papers using copper catalysts alone, see:
  • 5a Bohlmann F. Weber R. Chem. Ber.  1972,  105:  3036 
    Google Scholar
  • 5b Fallis AG. Hearn MTW. Jones ERH. Thaller V. Turner JL. J. Chem. Soc.  1973,  743 
    Google Scholar
  • 5c Rösner M. Köbrich G. Angew. Chem., Int. Ed. Engl.  1975,  14:  708 
    Google Scholar
  • 5d Villemin D. Cadiot P. Kuétegan M. Synthesis  1983,  230 
    Google Scholar
  • 5e Naemura K. Hokura Y. Nakazaki M. Tetrahedron  1986,  42:  1763 
    Google Scholar
  • 5f Alami M. Ferri F. Tetrahedron Lett.  1996,  37:  2763 
    Google Scholar
  • 5g Barbu E. Tsibouklis J. Tetrahedron Lett.  1996,  37:  5023 
    Google Scholar
  • 5h Grandjean D. Pale P. Chuche J. Tetrahedron Lett.  1992,  33:  5355 
    Google Scholar
  • 5i Ohba S. Engbersen JFJ. Tetrahedron  1991,  47:  9947 
    Google Scholar
  • 5j Mowery MD. Evans CE. Tetrahedron Lett.  1997,  38:  11 
    Google Scholar
  • 5k Gung BW. Dickson H. Org. Lett.  2002,  4:  2517 
    Google Scholar
  • 5l Gung BW. Kumi G. J. Org. Chem.  2003,  68:  5956 
    Google Scholar
  • For representative papers using copper and palladium co-catalysts, see:
  • 6a Kitamura T. Tanaka T. Taniguchi H. Stang PJ. J. Chem. Soc., Perkin Trans. 1  1991,  2892 
    Google Scholar
  • 6b Wityak J. Chan JB. Synth. Commun.  1991,  21:  977 
    Google Scholar
  • 6c Elbaum D. Nguyen TB. Jorgensen WL. Schreiber SL. Tetrahedron  1994,  50:  11503 
    Google Scholar
  • 6d Amatore C. Blart E. Genêt JP. Jutand A. Lemaire-Audoire S. Savignac M. J. Org. Chem.  1995,  60:  6829 
    Google Scholar
  • 6e Siegel K. Brückner R. Synlett  1999,  1227 
    Google Scholar
  • 6f Kim S. Kim S. Lee T. Ko H. Kim D. Org. Lett.  2004,  6:  3601 
    Google Scholar
  • 7a Shen W. Thomas S. Org. Lett.  2000,  2:  2857 
    Google Scholar
  • 7b Shi Shun ALK. Chernick ET. Eisler S. Tykwinski RR. J. Org. Chem.  2003,  68:  1339 
    Google Scholar
  • 7c Luu T. Tykwinski RR. J. Org. Chem.  2006,  71:  8982 
    Google Scholar
  • For selected papers for Pd-catalyzed homocoupling of terminal alkynes, see:
  • 8a Lei A. Srivastava M. Zhang X. J. Org. Chem.  2002,  67:  1969 
    Google Scholar
  • 8b Li J.-H. Liang Y. Zhang X.-D. Tetrahedron  2005,  61:  1903 
    Google Scholar
  • 8c Batsanov AS. Collings JC. Fairlamb IJS. Holland JP. Howard JAK. Lin Z. Marder TB. Parsons AC. Ward RC. Zhu J. J. Org. Chem.  2005,  70:  703 
    Google Scholar
  • 8d Li J.-H. Liang Y. Wang D.-P. Liu W.-J. Xie Y.-X. Yin D.-L. J. Org. Chem.  2005,  70:  2832 ; and references cited therein
    Google Scholar
  • 9a Hollins RA. Campos MPA. J. Org. Chem.  1979,  44:  3931 
    Google Scholar
  • 9b Heasley VL. Shellhamer DF. Heasley LE. Yaeger DB. J. Org. Chem.  1980,  45:  4649 
    Google Scholar
  • 9c Duan J. Dolbier WR. Chen Q.-Y. J. Org. Chem.  1998,  63:  9486 
    Google Scholar
  • 9d Pagni RM. Kabalka GW. Boothe R. Gaetano K. Stewart LJ. Conaway R. Dial C. Gray D. Larson S. Luidhardt T. J. Org. Chem.  1988,  53:  4477 
    Google Scholar
  • 9e Barluenga J. Montserrat JM. Florez J. J. Org. Chem.  1993,  58:  5976 
    Google Scholar
  • 9f Hénaff N. Whiting A. J. Chem. Soc., Perkin Trans. 1  2000,  395 
    Google Scholar
  • 9g Li J.-H. Xie Y.-X. Yin D.-L. Green Chem.  2002,  4:  505 
    Google Scholar
  • 9h Li J.-H. Xie Y.-X. Yin D.-L. Chin. J. Org. Chem.  2002,  22:  894 
    Google Scholar
  • For papers on the Heck reaction of (E)-1,2-diiodoalkenes with alkenes:
  • 10a Ranu BC. Chattopadhyay K. Org. Lett.  2007,  9:  2409 
    Google Scholar
  • 10b Ranu BC. Adak L. Chattopadhyay K. J. Org. Chem.  2008,  73:  5609 
    Google Scholar
  • 11 Aitken RA. Seth S. Synlett  1990,  212 
    Article in Thieme ConnectGoogle Scholar
  • 12 Balova IA. Sorokoumov VN. Morozkina SN. Vinogradova OV. Knight DW. Vasilevsky SF. Eur. J. Org. Chem.  2005,  882 
    CrossrefGoogle Scholar
  • 13 Kabalka GW. Wang L. Pagni RM. Synlett  2001,  108 
    Google Scholar
  • 14 Wan S. Yang S. Zhiwu Baohu Xuebao  2004,  31:  299 ; Chem. Abstr. 2004, 143, 207550
    Google Scholar
  • 15 Muckensturm B. Riss BP. Robert PC. Simonis MT. Kienlen JC. Biochem. Syst. Ecol.  1986,  14:  123 ; Chem. Abstr. 1986, 104, 220754
    CrossrefGoogle Scholar
  • 16 Tsuge O. Ueno K. Oe K. Chem. Lett.  1981,  135 
    CrossrefGoogle Scholar