Synthesis, structure, and reactivity of fully aryl-substituted pyrroles: toward the synthesis of nitrogen-doped buckybowls

Abstract

This study describes the synthesis and potential applications of pentaaryl-substituted pyrroles. We report a Pd-catalyzed approach for their preparation from 4,5-diyne-9-fluorenone (1,7-diyne) and aromatic amines. The target nitrogen-doped corannulenes (CO-hub-Ncor) were investigated computationally to understand their electronic properties. While the conversion of pyrroles to CO-hub-Ncor is underway, the pyrroles themselves hold promise as valuable building blocks for N-doped buckybowls. Additionally, the synthesized pyrrole derivatives exhibit interesting reactivity, including pyrrole oxidation, leading to a ring-opening product, specifically a dicarbonyl compound.