Palladium-Catalyzed 2-Arylation of Pyrroles

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Abstract
A methodology that affords N-alkyl-2-arylpyrroles and N-aryl-2-arylpyrroles via direct coupling from aryl iodides has been developed. After examining various reaction parameters: solvent, ratio of reagents, catalyst, base and additives the optimal conditions for the condensation were identified. Two crucial factors, (a) anhydrous DMSO as solvent and (b) 5 M excess of pyrrole counterpart, were found to strongly influence the reaction outcome. The conditions identified (PdCl2(PPh3)2, AgOAc, anhyd DMSO, KF, 100 °C, 5 h) resulted in the formation of 2-arylpyrroles in 14−80% yield. Furthermore, the synthesis is compatible with electron-withdrawing and electron-donating groups on the aryl moiety.

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