Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative
Amal Hassan Tolba, Martin Krupička, Josef Chudoba, Radek Cibulka
Abstract
We report an effective, operationally simple, and environmentally friendly system for the synthesis of tertiary amides by the oxidative coupling of aromatic or aliphatic aldehydes with amines mediated by riboflavin tetraacetate (RFTA), an inexpensive organic photocatalyst, and visible light using oxygen as the sole oxidant. The method is based on the oxidative power of an excited flavin catalyst and the relatively low oxidation potential of the hemiaminal formed by amine to aldehyde addition.
Topics & Concepts
ChemistryHemiaminalCatalysisAldehydeFlavin groupAmideRiboflavinMolecular oxygenOxidative coupling of methaneAmine gas treatingPhotochemistryOxidative phosphorylationOrganic chemistryPeptide bondDerivative (finance)PhotocatalysisCombinatorial chemistryEconomicsFinancial economicsBiochemistryEnzymeChemical Synthesis and AnalysisRadical Photochemical ReactionsSulfur-Based Synthesis Techniques