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Palladium Catalyzed, Multicomponent Synthesis of Fused-Ring Pyrroles from Aryl Iodides, Carbon Monoxide, and Alkyne-Tethered Imines

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journal contribution
posted on 11.10.2016, 00:00 by Neda Firoozi, Gerardo M. Torres, Bruce A. Arndtsen
A palladium-catalyzed multicomponent route to polycyclic pyrroles is described. Pd­(PtBu3)2 was 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.

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