Palladium-Catalyzed <i>anti</i>-Michael-Type (Hetero)arylation of Acrylamides
Hirotsugu Suzuki, Ryota Moro, Takanori Matsuda
Abstract
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 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.
Topics & Concepts
ChemistryPalladiumCatalysisMichael reactionCombinatorial chemistryOrganic chemistryMedicinal chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSulfur-Based Synthesis Techniques