title: One-Pot Amide Bond Formation from Aldehydes and Amines via a Photoorganocatalytic Activation of Aldehydes.
abstract: A mild, one-pot, and environmentally friendly synthesis of amides from aldehydes and amines is described. Initially, a photoorganocatalytic reaction of aldehydes with di-isopropyl azodicarboxylate leads to an intermediate carbonyl imide, which can react with a variety of amines to afford the desired amides. The initial visible light-mediated activation of a variety of monosubstituted or disubstituted aldehydes is usually fast, occurring in a few hours. Following the photocatalytic reaction, addition of the primary amine at room temperature or the secondary amine at elevated temperatures leads to the corresponding amide from moderate to excellent yields without epimerization. This methodology was applied in the synthesis of Moclobemide, a drug against depression and social anxiety.
authors.affiliation: Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodestrian University of Athens , Panepistimiopolis 15771, Athens, Greece.
authors.forename: Giorgos N
authors.initials: GN
authors.lastname: Papadopoulos
authors.affiliation: Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodestrian University of Athens , Panepistimiopolis 15771, Athens, Greece.
authors.forename: Christoforos G
authors.initials: CG
authors.lastname: Kokotos
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D020912:Moclobemide / Q000138:chemical synthesis
chemical_list: D000447:Aldehydes; D000577:Amides; D000588:Amines; D020912:Moclobemide