Palladium-Catalyzed -Michael-Type (Hetero)arylation of Acrylamides.

J Am Chem Soc

Department of Applied Chemistry, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.

Published: May 2024

This paper reports a direct α-(hetero)arylation of acrylamides through an inverse electron-demand nucleophilic addition, specifically an -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 β-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.

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http://dx.doi.org/10.1021/jacs.4c00841DOI Listing

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