title: Palladium Catalyzed, Multicomponent Synthesis of Fused-Ring Pyrroles from Aryl Iodides, Carbon Monoxide, and Alkyne-Tethered Imines.
abstract: A palladium-catalyzed multicomponent route to polycyclic pyrroles is described. Pd(PtBu3)2was found to catalyze the coupling of (hetero)aryl iodides, two equivalents of carbon monoxide and alkyne-tethered imines into 1,3-dipoles (Münchnones), which undergo spontaneous, intramolecular 1,3-dipolar cycloaddition to form polycyclic pyrroles. The systematic variation of the alkyne, tethered-imine, or aryl iodide can allow the buildup of a range of pyrrole derivatives, where any of the substituents can be independently varied. In addition, the same palladium catalyst can be employed in an initial Sonogashira-type coupling with aryl iodides, which upon the addition of CO can allow the novel tandem catalytic, five component synthesis of diversely substituted products.
authors.affiliation: Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.|Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad , Mashhad 9177948974, Iran.
authors.forename: Neda
authors.initials: N
authors.lastname: Firoozi
authors.affiliation: Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.
authors.forename: Gerardo M
authors.initials: GM
authors.lastname: Torres
authors.affiliation: Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.
authors.forename: Bruce A
authors.initials: BA
authors.lastname: Arndtsen