1O2 Mediated Conversion of ß-Enaminonitriles to α-Keto Amides Photosensitized by Recyclable H2TPP in Visible Light.
J Org Chem
; 89(7): 4722-4732, 2024 Apr 05.
Article
en En
| MEDLINE
| ID: mdl-38502937
ABSTRACT
We report a one-step approach for the conversion of ß-enaminonitriles to synthetically versatile α-keto amides in moderate to high yields under visible light irradiation photosensitized by porphyrins. The method is mild, cost-effective, and sustainable and requires air as the sole reagent/oxidant. The reaction is believed to proceed via an ene-type pathway initiated by 1O2, followed by dehydration, imine hydrolysis, and subsequent nucleophilic substitution of the cyanide group by amine. The method offers a broad substrate scope and has also been extended for synthesis of α-keto esters with aliphatic alcohols as nucleophiles. The porphyrin recovered after the reaction can be reused multiple times.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2024
Tipo del documento:
Article
País de afiliación:
India