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The first palladium-catalyzed, ligand-controlled chemoselective synthesis of imides has been achieved. An orthogonal set of conditions has been developed for multicomponent reaction of various olefin-tethered aryl iodides, isocyanides, and carboxylic… Click to show full abstract
The first palladium-catalyzed, ligand-controlled chemoselective synthesis of imides has been achieved. An orthogonal set of conditions has been developed for multicomponent reaction of various olefin-tethered aryl iodides, isocyanides, and carboxylic acids. Alkylimides ("cyclization on" products) via arylimidation of tethered unactivated alkenes and aryl imides ("cyclization off" products) via direct imidation of aryl iodides were obtained in good to excellent yields with good to excellent selectivity. Computational studies were performed to gain insight into the origin of the high levels of chemoselectivity observed.
Journal Title: Organic letters
Year Published: 2020
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