Synthesis 2012(7): 1030-1036  
DOI: 10.1055/s-0031-1289723
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Cu(acac)2-Catalyzed Synthesis of Functionalized Bis(arylmethyl)zinc Reagents and Their Olefination Reaction with Aromatic Aldehydes

Ying Fu*, Xuemei Hu, Yaojuan Chen, Yanshou Yang, Hongxia Hou, Yulai Hu
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, 730070, P. R. of China
Fax: +86(931)7768159; e-Mail: fuying@iccas.ac.cn;
Weitere Informationen

Publikationsverlauf

Received 17 December 2011
Publikationsdatum:
24. Februar 2012 (online)

Abstract

An efficient and facile copper(II) acetylacetonate catalyzed synthesis of functionalized bis(arylmethyl)zinc reagents from arylmethyl halides and their olefination reaction with aromatic aldehydes is reported. Aluminum trichloride was found to be the key ingredient in these reactions and (E)-stilbenes were obtained in high yields.

    References

  • 1a The Chemistry of Organozinc Compounds   Rappoport Z. Marek I. John Wiley & Sons; Chichester: 2006. 
  • 1b Knochel P. Jones P. Organozinc Reagents, A Practical Approach   Oxford University Press; Oxford: 1999. 
  • 1c Erdik E. Organozinc Reagents in Organic Synthesis   CRC Press; New York: 1996. 
  • 1d Knochel P. Handbook of Functionalized Organometallics   Wiley-VCH; Weinheim: 2005.  Chap. 7.
  • 2a Wang J.-X. Fu Y. Hu YL. Angew. Chem. Int. Ed.  2002,  41:  2757 
  • 2b Wang J.-X. Fu Y. Hu YL. Synthesis  2003,  1506 
  • 2c Wang J.-X. Wang K. Zhao L. Li H. Fu Y. Hu Y. Adv. Synth. Catal.  2006,  348:  1262 
  • 3 Knochel P. Synlett  1995,  393 
  • 4 Frankland E. Justus Liebigs Ann. Chem.  1849,  71:  171 
  • 5 Rozema MJ. Sidduri A. Knochel P. J. Org. Chem.  1992,  57:  1956 
  • 6a Langer F. Schwink L. Devasagayaraj A. Chavant P.-Y. J. Org. Chem.  1996,  61:  8229 
  • 6b Boudier A. Darcel C. Flachsmann F. Micouin L. Oestreich M. Knochel P. Chem. Eur. J.  2000,  6:  2748 
  • 6c Hupe E. Calaza MI. Knochel P. Chem. Eur. J.  2003,  9:  2789 
  • 7a Klement I. Lütjens H. Knochel P. Tetrahedron Lett.  1995,  36:  3161 
  • 7b Gao Y. Urabe H. Sato F. J. Org. Chem.  1994,  59:  5521 
  • 8a Nützel K. Houben--Weyl   4th Ed., Vol. 13/2a:  Georg Thieme Verlag; Stuttgart: 1973.  p.552 
  • 8b Von dem Bussche-Hünnefeld JL. Seebach D. Tetrahedron  1992,  48:  5719 
  • 8c Murakami K. Yorimitsu H. Oshima K. Chem. Eur. J.  2010,  16:  7688 
  • 8d Luche J.-L. Petrier C. Lansard J.-P. Greene AE. J. Org. Chem.  1983,  48:  3837 
  • 8e Luzung MR. Patel JS. Yin J. J. Org. Chem.  2010,  75:  8330 
  • 9a Metzger A. Bernhardt S. Manolikakes G. Knochel P. Angew. Chem. Int. Ed.  2010,  49:  4665 
  • 9b Buesking AW. Baguley TD. Ellman JA. Org. Lett.  2011,  13:  964 
  • 9c Metzger A. Piller FM. Knochel P. Chem. Commun.  2008,  5824 
  • 10 Buesking AW. Baguley TD. Ellman JA. Org. Lett.  2011,  13:  964 
  • 11 Eastham JF. Cannon DY. J. Org. Chem.  1960,  25:  1504 
  • 12 Peng Z.-Y. Ma F.-F. Zhu L.-F. Xie X.-M. Zhang Z.
    J. Org. Chem.  2009,  74:  6855 
  • 13 Knoess HP. Furlong MT. Rozema MJ. Knochel P.
    J. Org. Chem.  1991,  56:  5974 
  • 14 Sugihara T. Satoh T. Miura M. Nomura M. Adv. Synth. Catal.  2004,  346:  1765 
  • 15 Wadsworth WS. Emmons WD. J. Am. Chem. Soc.  1961,  83:  1733 
  • 16 Yasuda M. Isami T. Kubo J. Mizutani M. Yamashita T. Shima K. J. Org. Chem.  1992,  57:  1351 
  • 17 Chhor RB. Singh KA. Nosse B. Tandon VK. Synth. Commun.  2003,  33:  2519 
  • 18 Kim C.-B. Cho C.-H. Jo MJ. Park K. Bull. Korean Chem. Soc.  2011,  32:  3655 
  • 19 von Walter R. Wetzlich A. J. Prakt. Chem.  1900,  61:  169 
  • 20 Ruasse MF. Dubois JE. J. Org. Chem.  1972,  37:  1770