RESUMO
Here we report a palladium-catalyzed anti-Michael-type hydroamination of N-(quinolin-8-yl)acrylamide with 2-pyridones. The use of a palladium catalyst enables the α-addition of 2-pyridones, resulting in the formation of a range of N-substituted 2-pyridone carboxamides with yields ranging from 10% to 80%. Derivatization of the products highlights the utility of this transformation. Preliminary mechanistic investigations suggest that the reaction proceeds through the direct addition of a nitrogen atom of 2-pyridones, ruling out other pathways such as O-to-N-alkyl migration.
RESUMO
This paper reports a direct α-(hetero)arylation of acrylamides through an inverse electron-demand nucleophilic addition, specifically an anti-Michael-type addition. The introduction of a quinolyl directing group facilitates the nucleophilic addition of (hetero)arenes to the α-position of acrylamides. The quinolyl directing group effectively suppresses undesired ß-hydrogen elimination and is removable for subsequent derivatization. The presented method provides an atom economical synthesis of α-(hetero)arylamide with a high degree of functional group tolerance.
