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. - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2012

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.

Jean-Baptiste Gualtierotti
  • Fonction : Auteur
Xavier Schumacher
  • Fonction : Auteur
Patrice Fontaine
Qian Wang
Jieping Zhu
  • Fonction : Auteur

Résumé

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.

Domaines

Chimie organique

Dates et versions

hal-00763836 , version 1 (11-12-2012)

Identifiants

Citer

Jean-Baptiste Gualtierotti, Xavier Schumacher, Patrice Fontaine, Géraldine Masson, Qian Wang, et al.. 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.. Chemistry - A European Journal, 2012, 18 (46), pp.14812-9. ⟨10.1002/chem.201202291⟩. ⟨hal-00763836⟩
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