A palladium-catalyzed synthesis of (hetero) aryl-substituted imidazoles from aryl halides, imines and carbon monoxide
Tjutrins, J.; Arndtsen, B.A.
Chemical Science 8(2): 1002-1007
ISSN/ISBN: 2041-6520 PMID: 28451237 DOI: 10.1039/c6sc04371b
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.