Bis-arylation of Phenylene-bridged Bis-azolium salts and Tetra-arylation of Bis-azoles to Access Symmetrical and Unsymmetrical CCC-aNHC Pincer Ligand Precursors
ORCID
MSU Affiliation
College of Arts and Sciences; Department of Chemistry
Creation Date
2025-12-11
Abstract
Copper-mediated methodologies for the arylation of bis-azolium salts and bis-azoles are efficient pathways to access symmetrical and unsymmetrical N-heterocyclic carbene precursors. The arylation of bis-azolium salts with various aryl halides was achieved in moderate yields to furnish numerous C2-arylated bis-azolium salts. Access of C2-arylated bis-azolium salts from bis-azoles was also achieved in a single pot domino reaction via the use of iodonium salts as embedded electrophiles. The latter methodology utilizes the aryl iodide byproduct from the N-arylation step for the C–H activation step to mitigate waste and the need to recycle. We also demonstrated the use of these azolium salts in metalation and found success in obtaining metal complexes containing abnormal N-heterocyclic carbenes.
Publication Date
11-11-2025
Publication Title
Tetrahedron
Publisher
Elsevier
Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.
Recommended Citation
Cecil, A. C., Fosu, E., Donnadieu, B., & Hollis, T. K. (2026). Bis-arylation of phenylene-bridged bis-azolium salts and tetra-arylation of bis-azoles to access symmetrical and unsymmetrical CCC-aNHC pincer ligand precursors. Tetrahedron, 190, 135045. https://doi.org/10.1016/j.tet.2025.135045
