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Synthesis 2010(24): 4188-4192  
DOI: 10.1055/s-0030-1258287
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Samarium-Promoted Michael Addition between Aroyl Chlorides and Chalcones

Yongjun Liu, Yuanying Li, Yan Qi, Jun Wan*
State Key Laboratory Base of Eco-chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China
Fax: +86(532)84023927; e-Mail: wanjundz@sohu.com;
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Publikationsverlauf

Received 26 July 2010
Publikationsdatum:
07. Oktober 2010 (online)

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Abstract

A novel Michael addition type reaction between aroyl chlorides and chalcones was realized in the presence of samarium metal when N,N-dimethylformamide was used as a solvent. A variety of 1,4-diketones were thereby synthesized in moderate to good yields. The possible mechanism is also discussed.

Key words

samarium - Michael addition - aroyl chlorides - chalcones - 1,4-diketones

    References

  • For recent reports on the application of the Michael addition in organic synthesis, see:
  • 1a Xia X.-F. Shu X.-Z. Ji K.-G. Yang Y.-F. Shaukat A. Liu X.-Y. Liang Y.-M. J. Org. Chem.  2010,  75:  2893 
    Google Scholar
  • 1b Attanasi OA. Favi G. Filippone P. Mantellini F. Moscatelli G. Perrulli FR. Org. Lett.  2010,  12:  468 
    Google Scholar
  • 1c Luna LE. Seoane G. Cravero RM. Eur. J. Org. Chem.  2008,  1271 
    Google Scholar
  • 1d Kazmaier U. Angew. Chem. Int. Ed.  2009,  48:  5790 
    Google Scholar
  • 2a Bower J. Box MR. Czyzewski M. Goeta AE. Steel PG. Org. Lett.  2009,  11:  2744 
    Google Scholar
  • 2b Mattson AE. Bharadwaj AR. Scheidt KA. J. Am. Chem. Soc.  2004,  126:  2314 
    Google Scholar
  • 2c Mattson AE. Bharadwaj AR. Zuhl AM. Scheidt KA. J. Org. Chem.  2006,  71:  5715 
    Google Scholar
  • 2d Han Z. Fujioka T. Usugi S.-i. Yorimitsu H. Shinokubo H. Oshima K. Org. Biomol. Chem.  2005,  3:  1622 
    Google Scholar
  • 2e Ohno T. Sakai M. Ishino Y. Shibata T. Maekawa H. Nishiguchi I. Org. Lett.  2001,  3:  3439 
    Google Scholar
  • For examples, see:
  • 3a Menard F. Weise CF. Lautens M. Org. Lett.  2007,  9:  5365 
    Google Scholar
  • 3b Demir AS. Reis Ö. Igdir AÇ. Esiringü I. Eymur S. J. Org. Chem.  2005,  70:  10584 
    Google Scholar
  • 3c Hashimoto T. Hirose M. Maruoka K. J. Am. Chem. Soc.  2008,  130:  7556 
    Google Scholar
  • 4a Sun F.-G. Huang X.-L. Ye S. J. Org. Chem.  2010,  75:  273 
    Google Scholar
  • 4b Sánchez-Larios E. Gravel M. J. Org. Chem.  2009,  74:  7536 
    Google Scholar
  • 4c DiRocco DA. Oberg KM. Dalton DM. Rovis T. J. Am. Chem. Soc.  2009,  131:  10872 
    Google Scholar
  • 4d Liu Q. Rovis T. Org. Lett.  2009,  11:  2856 
    Google Scholar
  • 4e Christmann M. Angew. Chem. Int. Ed.  2005,  44:  2632 
    Google Scholar
  • 5 Hassner A. In Comprehensive Organic Synthesis   Vol. 1:  Trost BM. Pergamon Press; Oxford: 1991.  p.541-577  
    Google Scholar
  • 6a Nicolaou KC. Ellery SP. Chen JS. Angew. Chem. Int. Ed.  2009,  48:  7140 
    Google Scholar
  • 6b Procter DJ. Flowers RA. Skrydstrup T. Organic Synthesis Using Samarium Diiodide: A Practical Guide   Royal Society of Chemistry Publishing; Cambridge: 2009. 
    Google Scholar
  • 6c Flowers RA. Synlett  2008,  1427 
    Google Scholar
  • 6d Edmonds DJ. Johnston D. Procter DJ. Chem. Rev.  2004,  104:  3371 
    Google Scholar
  • 7 For a review of the use of metallic samarium, see: Banik BK. Eur. J. Org. Chem.  2002,  2431 
    CrossrefGoogle Scholar
  • 8a Ghatak A. Becker FF. Banik BK. Tetrahedron Lett.  2000,  41:  3793 
    Google Scholar
  • 8b Talukdar S. Fang J.-M. J. Org. Chem.  2001,  66:  330 
    Google Scholar
  • For example, see:
  • 9a Liu Y. Zhang F. Qi Y. Zhang Y. Zhang S. Eur. J. Org. Chem.  2008,  5470 
    Google Scholar
  • 9b Liu Y. Xu X. Zhang Y. Synlett  2004,  445 
    Google Scholar
  • 9c Liu Y. Zhang Y. Tetrahedron Lett.  2004,  45:  1295 
    Google Scholar
  • 9d Liu Y. Zhang Y. Tetrahedron  2003,  59:  8429 
    Google Scholar
  • 10a Liu Y. Wang X. Zhang Y. Synth. Commun.  2004,  34:  4009 
    Google Scholar
  • 10b Liu Y. Dai N. Qi Y. Zhang S. Synth. Commun.  2009,  39:  799 
    Google Scholar
  • 11a Ujikawa O. Inanaga J. Yamaguchi M. Tetrahedron Lett.  1989,  30:  2837 
    Google Scholar
  • 11b Inanaga J. Katsuki J. Ujikawa O. Yamaguchi M. Tetrahedron Lett.  1991,  32:  4921 
    Google Scholar
  • For example, see:
  • 12a Wilson DC. Liu S. Chen X. Meyers EA. Bao X. Prosvirin AV. Dunbar KR. Hadad CM. Shore SG. Inorg. Chem.  2009,  48:  5725 
    Google Scholar
  • 12b Ishiguro S. Takahashi R. Ozutsumi K. Kidorui  1994,  24:  96 ; Chem. Abstr. 1994, 121, 118731j
    Google Scholar
  • 12c Hanawa H. Kii S. Asao N. Maruoka K. Tetrahedron Lett.  2000,  41:  5543 
    Google Scholar