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

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