Abstract
N-Substituted aromatic and heteroaromatic amides reacted with substituted allylic alcohols in the presence of a ruthenium catalyst, AgSbF6 and a Cu(OAc)2·H2O oxidant, affording 3-substituted isoindolinone derivatives with diverse substituents in good to excellent yields. A possible reaction mechanism involving a five-membered ruthenacycle intermediate was proposed and strongly supported by experimental evidence.
Highlights
N-Substituted aromatic and heteroaromatic amides reacted with substituted allylic alcohols in the presence of a ruthenium catalyst, AgSbF6 and a Cu(OAc)2ÁH2O oxidant, affording 3-substituted isoindolinone derivatives with diverse substituents in good to excellent yields
Aromatic imines underwent cyclization with isocyanates in the presence of a rhenium catalyst, providing 3-substituted isoindolinones.8a N-Substituted benzamides reacted with alkenes in the presence of metal catalysts, giving isoindolinones in good to excellent yields.8b–g In the reaction, mostly activated alkenes such as acrylates, ethyl vinyl ketone, acrylamide and conjugated 1,2-diketones were used.[8]
Allylic alcohols have been efficiently used as coupling partners in the reaction with heteroatom substituted aromatics, and this transformation leads to ortho alkylated aromatics in the presence of metal catalysts via C–H bond activation.[10]
Summary
N-Substituted aromatic and heteroaromatic amides reacted with substituted allylic alcohols in the presence of a ruthenium catalyst, AgSbF6 and a Cu(OAc)2ÁH2O oxidant, affording 3-substituted isoindolinone derivatives with diverse substituents in good to excellent yields. Allylic alcohols have been efficiently used as coupling partners in the reaction with heteroatom substituted aromatics, and this transformation leads to ortho alkylated aromatics in the presence of metal catalysts via C–H bond activation.[10] we report a ruthenium-catalyzed cyclization of N-substituted benzamides with allylic alcohols to give 3-substituted isoindolinone derivatives in good yields.
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