Elsevier

Tetrahedron Letters

Volume 48, Issue 1, 1 January 2007, Pages 141-143
Tetrahedron Letters

Significant rate acceleration of the aza-Michael reaction in water

https://doi.org/10.1016/j.tetlet.2006.10.142Get rights and content

Abstract

The addition of amines to conjugated alkenes has been carried out in water at room temperature very efficiently without any catalyst. Significant rate acceleration of this reaction is observed in water compared to organic solvents.

Graphical abstract

Remarkable rate acceleration is reported for the aza-Michael reaction in water at room temperature in the absence of any catalyst or co-organic solvent.

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Acknowledgements

We are pleased to acknowledge the financial support from CSIR [Grant No. 01(1936)/04/EMR-1]. S.B. also thanks CSIR for his fellowship.

References and notes (15)

  • C. Southwick

    J. Am. Chem. Soc.

    (1953)
  • A.K. Verma et al.

    Tetrahedron Lett.

    (2005)
  • C.J. Li et al.
  • N. Azizi et al.

    Org. Lett.

    (2005)
    N. Azizi et al.

    J. Org. Chem.

    (2006)
    G.L. Khatik et al.

    Org. Lett.

    (2006)
  • G. Bartoli et al.

    J. Org. Chem.

    (1994)
    Y. Hayashi et al.

    J. Am. Chem. Soc.

    (1996)
  • G. Cardillo et al.

    Chem. Soc. Rev.

    (1996)
    E. Hagiwara et al.

    J. Am. Chem. Soc.

    (1998)
There are more references available in the full text version of this article.

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    Citation Excerpt :

    Subsequently, the enol form tautomerizes to aza-Michael adduct with the aid of multiple water molecules. As mentioned in the mechanistic pathway, the transfer of hydrogen could proceed with the assistance of water molecule smoothly because the water molecules activate both amine and olefin by increasing the nucleophilic and electrophilic character respectively, which supports the assumption that the studied aza-Michael additions proceed via the water assisted transition states [36]. Thus, we have established the feasibility of conjugate addition of amines (both 1° and 2°) to various acrylamides, acrylonitrile, vinyl ketone etc in water without any external catalytic assistance.

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