Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative

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 ox...

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Bibliographic Details
Published in:Organic letters 2021-09, Vol.23 (17), p.6825-6830
Main Authors: Hassan Tolba, Amal, Krupička, Martin, Chudoba, Josef, Cibulka, Radek
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Amides - chemical synthesis
Amides - chemistry
Amines - chemistry
Molecular Structure
Oxidation-Reduction
Riboflavin - analogs & derivatives
Riboflavin - chemical synthesis
Riboflavin - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02391