Palladium-Catalyzed Chemodivergent Carbonylation of ortho-Bromoarylimine to Biisoindolinones and Spiroisoindolinones

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.

Automated summary

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.