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.
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.
authors.affiliation: Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH, Switzerland.
authors.forename: Jean-Baptiste
authors.initials: JB
authors.lastname: Gualtierotti
authors.forename: Xavier
authors.initials: X
authors.lastname: Schumacher
authors.forename: Patrice
authors.initials: P
authors.lastname: Fontaine
authors.forename: Géraldine
authors.initials: G
authors.lastname: Masson
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000537:Aluminum Oxide / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006868:Hydrolysis; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010084:Oxidation-Reduction; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000447:Aldehydes; D000588:Amines; C406102:N-mercaptoamide; D009570:Nitriles; D013438:Sulfhydryl Compounds; D000537:Aluminum Oxide