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Synthesis 2011(2): 325-329  
DOI: 10.1055/s-0030-1258365
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Polystyrene-Supported Zinc Bromide-Ethylenediamine Complex as a Reusable and Highly Efficient Heterogeneous Catalyst for the Synthesis of α,β-Acetylenic Ketones

Ali Keivanloo*, Mohammad Bakherad, Bahram Bahramian, Mahrokh Rahmani, Sayed Ali Naghi Taheri
School of Chemistry, Shahrood University of Technology, Shahrood, Iran
Fax: +98(273)3395441; e-Mail: akeivanloo@yahoo.com; e-Mail: keivanloo@shahroodut.ac.ir;
Further Information

Publication History

Received 4 October 2010
Publication Date:
15 December 2010 (online)

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Abstract

A polystyrene-supported zinc bromide-ethylenediamine complex was shown to be useful as a recyclable heterogeneous catalyst for the rapid and efficient synthesis of α,β-acetylenic ketones in good-to-excellent yields by cross-coupling of acid chlorides with terminal alkynes. The catalyst is easily prepared, stable, reusable, and efficient under the reaction conditions.

Key words

heterogeneous catalysis - cross-coupling - acid chlorides - alkynes - ketones

    References

  • 1a Karpov AS. Müller TJJ. Org. Lett.  2003,  5:  3451 
    Google Scholar
  • 1b Van den Hoven BG. El Ali B. Alper H. J. Org. Chem.  2000,  65:  4131 
    Google Scholar
  • 1c Wang X.-J. Tan J. Zhang L. Org. Lett.  2000,  2:  3107 
    Google Scholar
  • 1d Kel’in AV. Sromek AW. Gevorgyan V. J. Am. Chem. Soc.  2001,  123:  2074 
    Google Scholar
  • 1e Bagley MC. Hughes DD. Lloyd R. Powers VEC. Tetrahedron Lett.  2001,  42:  6585 
    Google Scholar
  • 1f Bagley MC. Hughes DD. Taylor PH. Synlett  2003,  259 
    Google Scholar
  • 1g Karpov AS. Merkul E. Oeser T. Müller TJJ. Chem. Commun.  2005,  2581 
    Google Scholar
  • 1h Waldo JP. Larock RC. Org. Lett.  2005,  7:  5203 
    Google Scholar
  • 1i Karpov AS. Merkul E. Oeser T. Müller TJJ. Eur. J. Org. Chem.  2006,  13:  2991 
    Google Scholar
  • 1j Zhou C. Dubrovsky AV. Larock RC. J. Org. Chem.  2006,  71:  1626 
    Google Scholar
  • 2a Tohda Y. Sonogashira K. Hagihara N. Synthesis  1977,  777 
    Google Scholar
  • 2b Walton DRM. Waugh F. J. Organomet. Chem.  1972,  37:  45 
    Google Scholar
  • 2c Newman H. J. Org. Chem.  1973,  38:  2254 
    Google Scholar
  • 2d Yadav JS. Reddy BVS. Reddy MS. Synlett  2003,  1722 
    Google Scholar
  • 2e Wang J.-X. Wei B. Hu Y. Liu Z. Fu Y. Synth. Commun.  2001,  31:  3527 
    Google Scholar
  • 2f Cox RJ. Ritson DJ. Dane TA. Berge J. Charmant JPH. Kantacha A. Chem. Commun.  2005,  1037 
    Google Scholar
  • 2g Chen L. Li C.-J. Org. Lett.  2004,  6:  3151 
    Google Scholar
  • 2h Guo M. Li D. Zhang Z. J. Org. Chem.  2003,  68:  10172 
    Google Scholar
  • 3 Davis RB. Scheiber DH. J. Am. Chem. Soc.  1956,  78:  1675 
    Google Scholar
  • 4a Normant JF. Synthesis  1972,  63: 
    Google Scholar
  • 4b Logue MW. Moore GL. J. Org. Chem.  1975,  40:  131 
    Google Scholar
  • 4c Bourgain M. Normant JF. Bull. Soc. Chim. Fr.  1973,  2137 
    Google Scholar
  • 5 Fontaine M. Chauvelier J. Barchewitz P. Bull. Soc. Chim. Fr.  1962,  2145 
    Google Scholar
  • 6 Compagnon PL. Grosjean B. Lacour M. Bull. Soc. Chim. Fr.  1975,  779 
    Google Scholar
  • 7 Yashina OG. Zarva TV. Vereshchagin LI. Zh. Org. Khim.  1967,  3:  219 ; Chem. Abstr. 1967, 66, 94664g
    Google Scholar
  • 8 Vereshchagin LI. Yashina OG. Zarva TV. Zh. Org. Khim.  1966,  2:  1895 ; Chem. Abstr. 1967, 66, 46070p
    Google Scholar
  • 9 Walton DRM. Waugh F. J. Organomet. Chem.  1972,  37:  45 
    CrossrefGoogle Scholar
  • 10 Logue MW. Teng K. J. Org. Chem.  1982,  47:  2549 
    CrossrefGoogle Scholar
  • 11 Mohamed Ahmed MS. Mori A. Org. Lett.  2003,  5:  3057 
    CrossrefGoogle Scholar
  • 12a McNamara CA. Dixon MJ. Bradley M. Chem. Rev.  2002,  102:  3275 
    Google Scholar
  • 12b Clapham B. Reger TS. Janda KD. Tetrahedron  2001,  57:  4637 
    Google Scholar
  • 12c de Miguel YR. Brule E. Margue RG. J. Chem. Soc., Perkin Trans. 1  2001,  3085 
    Google Scholar
  • 12d Nishio R. Sugiura M. Kobayashi S. Chem. Asian J.  2007,  2:  983 
    Google Scholar
  • 12e Ye Z.-W. Yi W.-B. J. Fluorine Chem.  2008,  129:  1124 
    Google Scholar
  • 12f Chen L. Hong S. Zhou X. Zhou Z. Hou H. Catal. Commun.  2008,  9:  2221 
    Google Scholar
  • 13a Bakherad M. Keivanloo A. Bahramian B. Hashemi M. Tetrahedron Lett.  2009,  50:  1557 
    Google Scholar
  • 13b Bakherad M. Keivanloo A. Bahramian B. Mihanparast S. Tetrahedron Lett.  2009,  50:  6418 
    Google Scholar
  • 14a Bakherad M. Keivanloo A. Bahramian B. Rajaie M. Tetrahedron Lett.  2010,  51:  33 
    Google Scholar
  • 14b Bakherad M. Amin AH. Keivanloo A. Bahramian B. Raessi M. Chin. Chem. Lett.  2010,  21:  656 
    Google Scholar
  • 15a Chen J.-Y. Lin T.-C. Chen S.-C. Chen A.-J. Mou C.-Y. Tsai F.-Y. Tetrahedron  2009,  65:  10134 
    Google Scholar
  • 15b Palimkar SS. Kumar PH. Jogdand NR. Daniel T. Lahoti RJ. Srinivasan KV. Tetrahedron Lett.  2006,  47:  5527 
    Google Scholar
  • 15c Fukuyama T. Yamaura R. Ryu I. Can. J. Chem.  2005,  83:  711 
    Google Scholar
  • 15d Hao W. Sha J. Sheng S. Cai M.
    J. Mol. Catal. A: Chem.  2009,  298:  94 
    Google Scholar
  • 15e Liang B. Huang M. You Z. Xiong Z. Lu K. Fathi R. Chen J. Yang Z. J. Org. Chem.  2005,  70:  6097 
    Google Scholar
  • 15f Wang B. Bonin M. Micouin L. Org. Chem.  2005,  70:  6126 
    Google Scholar
  • 15g Nishihara Y. Saito D. Inoue E. Okada Y. Miyazaki M. Inoue Y. Takagi K. Tetrahedron Lett.  2010,  51:  306 
    Google Scholar