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A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide. 2017

Jevgenijs Tjutrins, and Bruce A Arndtsen
Department of Chemistry , McGill University , 801 Sherbrooke St. W. , Montreal , QC , Canada H3A 0B8 . Email: bruce.arndtsen@mcgill.ca ; ; Tel: +1-514-398-6999.

We describe here a tandem catalytic route to prepare imidazoles in a single operation from aryl iodides, imines and CO. The reaction involves a catalytic carbonylation of aryl halides with imines to form 1,3-dipoles, which undergo spontaneous 1,3-dipolar cycloaddition. Overall, this offers an alternative to coupling reactions to construct the (hetero)aryl-imidazole motif, where variation of the building blocks can allow the synthesis of broad families of imidazoles with independent control of all substituents.

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