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  • Title: Amidation of aldehydes and alcohols through α-iminonitriles and a sequential oxidative three-component Strecker reaction/thio-Michael addition/alumina-promoted hydrolysis process to access β-mercaptoamides from aldehydes, amines, and thiols.
    Author: Gualtierotti JB, Schumacher X, Fontaine P, Masson G, Wang Q, Zhu J.
    Journal: Chemistry; 2012 Nov 12; 18(46):14812-9. PubMed ID: 23019046.
    Abstract:
    Mild and general alumina-promoted hydrolysis conditions for converting α-iminonitriles into carboxamides have been developed. In combination with the oxidative three-component Strecker reaction, the one-pot direct amidation of aldehydes and alcohols is reported. Subsequently, an Yb(OTf)(3)-catalyzed Michael addition of thiols to α,β-unsaturated α-iminonitriles is reported for the synthesis of β-mercapto-α-iminonitriles. The successful integration of an oxidative Strecker reaction, thio-Michael addition, and neutral-alumina-promoted hydrolysis of β-mercapto-α-iminonitriles into a three-component one-pot process allowed us to develop the direct conversion of amines, aldehydes, and thiols into β-mercaptoamides. All of these procedures were applicable to aromatic and aliphatic amines and aldehydes.
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