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

Sha Yang; Jie Zhou; Ziyang Gan; Shuai Wu; Dan Shi; Hong Yan; Lili Xie; Jiajia Cheng; Yuanming Li

doi:10.1039/d4ob01835d

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

Org Biomol Chem. 2024 Dec 12. doi: 10.1039/d4ob01835d. Online ahead of print.

Authors

Sha Yang¹, Jie Zhou¹, Ziyang Gan², Shuai Wu², Dan Shi², Hong Yan², Lili Xie², Jiajia Cheng^{1

2}, Yuanming Li^{1

2}

Affiliations

¹ State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, 350116, China. jjcheng@fzu.edu.cn.
² Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China.

PMID: 39665416
DOI: 10.1039/d4ob01835d

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.