Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 8, Pages 5194-5204Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02170
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A palladium-catalyzed carbonylative cyclization reaction of ortho-bromoarylimines is reported, allowing for the chemodivergent synthesis of functionalized biisoindolinones and spirocyclic isoindolinones. By switching the reaction temperatures and ligands, either product could be selectively obtained, and the biisoindolinone products could be easily achieved with catalyst loadings as low as 0.05 mol%. Further transformation of the biisoindolinone product is also described, providing a novel and concise approach to the biisoindoline diamine ligand.
We herein report a palladium-catalyzed carbonylative cyclization reaction of ortho-bromoarylimines that allows for the chemodivergent synthesis of functionalized biisoindolinones and spirocyclic isoindolinones. Either product could be selectively obtained by switching the reaction temperatures and ligands, and the biisoindolinone products could be afforded facilely with catalyst loadings as low as 0.05 mol %. Further transformation of the biisoindolinone product is also described, which represents a novel and concise approach to the biisoindoline diamine ligand.
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