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Synthesis 2010(22): 3802-3810  
DOI: 10.1055/s-0030-1258314
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© Georg Thieme Verlag Stuttgart ˙ New York

Direct Addition of Functionalized Organozinc Reagents to Carbon Dioxide, Ketones, and Aldehydes in the Presence of MgCl2

Sebastian Bernhardt, Albrecht Metzger, Paul Knochel*
Ludwigs-Maximilians-Universität München, Department Chemie, Butenandtstraße 5-13, Haus F, 81377 München, Germany
Fax: +49(89)218077680; e-Mail: Paul.Knochel@cup.uni-muenchen.de;
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Publication History

Received 22 September 2010
Publication Date:
22 October 2010 (online)

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Abstract

A variety of functionalized organozinc reagents undergo smooth addition reactions at ambient temperature to carbon dioxide, ketones, and aldehydes in the presence of stoichiometric amounts of MgCl2. Several reactions were performed on a 20 mmol scale.

Key words

organozinc reagents - magnesium chloride - carbon dioxide - phenylacetic acid derivatives - addition reactions

    References

  • 1a The Chemistry of Organolithium Compounds   Rappoport Z. Marek I. Wiley; Chichester: 2004. 
    Google Scholar
  • 1b Wakefield BJ. The Chemistry of Organolithium Compounds   Pergamon Press; New York: 1974. 
    Google Scholar
  • 1c Noyori R. Kitamura M. Angew. Chem., Int. Ed. Engl.  1991,  30:  49 
    Google Scholar
  • 1d Tomioka K. Inoue I. Shindo M. Koga K. Tetrahedron Lett.  1990,  31:  6681 
    Google Scholar
  • 1e The Chemistry of Organomagnesium Compounds   Rappoport Z. Marek I. Wiley; Chichester: 2008. 
    Google Scholar
  • 1f Luderer MR. Bailey WF. Luderer MR. Fair JD. Dancer RJ. Sommer MB. Tetrahedron: Asymmetry  2009,  20:  981 
    Google Scholar
  • 2a Knochel P. Singer RD. Chem. Rev.  1993,  93:  2117 
    Google Scholar
  • 2b Knochel P. Millot N. Rodriguez A. Tucker CE. Org. React.  2001,  58:  417 
    Google Scholar
  • 2c Organozinc Reagents   Knochel P. Jones P. Oxford University Press; New York: 1999. 
    Google Scholar
  • 2d Krasovskiy A. Malakhov V. Gavryushin A. Knochel P. Angew. Chem. Int. Ed.  2006,  45:  6040 
    Google Scholar
  • 2e Metzger A. Schade MA. Knochel P. Org. Lett.  2008,  10:  1107 
    Google Scholar
  • 2f Metzger A. Argyo C. Knochel P. Synthesis  2010,  882 
    Google Scholar
  • For selected examples, see:
  • 3a Shi J. Zeng X. Negishi E. Org. Lett.  2003,  5:  1825 
    Google Scholar
  • 3b Gavryushin A. Kofink C. Manolikakes G. Knochel P. Org. Lett.  2005,  7:  4871 
    Google Scholar
  • 3c Yeh MCP. Knochel P. Santa LE. Tetrahedron Lett.  1988,  29:  3887 
    Google Scholar
  • 3d Reddy CK. Knochel P. Angew. Chem., Int. Ed. Engl.  1996,  35:  1700 
    Google Scholar
  • 3e Kazmierski I. Bastienne M. Gosmini C. Paris J.-M. Périchon J. J. Org. Chem.  2004,  69:  936 
    Google Scholar
  • 3f Dong Z. Manolikakes G. Li J. Knochel P. Synthesis  2009,  681 
    Google Scholar
  • 3g Monzon G. Knochel P. Synlett  2010,  304 
    Google Scholar
  • 3h Tamaru Y. Nakamura T. Sakaguchi M. Ochiai H. Yoshida Z. J. Chem. Soc., Chem. Commun.  1988,  610 
    Google Scholar
  • 3i Metzger A. Gavryushin A. Knochel P. Synlett  2009,  1433 
    Google Scholar
  • 3j Seebach D. Beck AK. Schmidt B. Wang YM. Tetrahedron  1994,  50:  4363 
    Google Scholar
  • 4a Piller FM. Appukkuttan P. Gavryushin A. Helm M. Knochel P. Angew. Chem. Int. Ed.  2008,  47:  6802 
    Google Scholar
  • 4b Piller FM. Metzger A. Schade MA. Haag BH. Gavryushin A. Knochel P. Chem. Eur. J.  2009,  15:  7192 
    Google Scholar
  • 5 Metzger A. Piller FM. Knochel P. Chem. Commun.  2008,  5824 
    CrossrefGoogle Scholar
  • 6 Blümke TD. Piller FM. Knochel P. Chem. Commun.  2010,  46:  4082 
    CrossrefGoogle Scholar
  • 7 Metzger A. Bernhardt S. Manolikakes G. Knochel P. Angew. Chem. Int. Ed.  2010,  49:  4665 
    CrossrefGoogle Scholar
  • 8 Krasovskiy A. Knochel P. Synthesis  2006,  890 
    Article in Thieme ConnectGoogle Scholar