Synthesis of N-alkenylisoquinolinones via palladium-catalyzed cyclization/C4-O bond cleavage of oxazolidines

A novel strategy for the synthesis of various N-alkenylisoquinolinones is reported, which features broad functional group tolerance, and good chemoselectivity. This reaction proceeds through sequential palladium-catalyzed cyclization and C4-O bond cleavage of oxazolidines to form carbon-carbon and carbon-oxygen double bonds. In addition, the practical value of this method has been explored by conducting a millimole reaction, as well as via the palladium-catalyzed C-H arylation and visible-light-assisted photocatalyzed conversion of the cyclic enamide to valuable compounds. © 2022 The Royal Society of Chemistry.