Bis-arylation of phenylene-bridged bis-azolium salts and tetra-arylation of bis-azoles to access symmetrical and unsymmetrical CCC-aNHC pincer ligand precursors
Year: 2025
Type: article
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 funish 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.
Source: Tetrahedron
Institution: Mississippi State University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $3,680
Awards: PFI-TT: Optimizing Next-Generation Materials for Organic Light Emitting Diode (OLED) Applications, Equipment: Helium Recovery Equipment: Efficient Recycling and Reuse of Liquid Helium in the Mississippi State University NMR Facility, G4900067765, MRI: Acquisition of the First 800 MHz NMR with Cryoprobe in the State of Mississippi for Biological and Chemical Research and Teaching, RII Track-2 FEC: Feeding and Powering the World - Capturing Sunlight to Split Water and Generate Fertilizer and Fuels, MRI: Track 1 Acquisition of a High-Resolution Quadrupole Time-of-Flight Mass Spectrometer with Diverse Inlet and Ionization Capabilities for Chemical Analyses
OpenAlex ID: W4415985388