Cross-coupling reactions are of great importance in chemistry due to their ability to facilitate the construction of complex organic molecules. Among these reactions, the Ullmann-type C−O coupling between phenols and aryl halides is particularly noteworthy and useful for preparing diarylethers. However, this reaction typically relies on homogeneous catalysts that rapidly deactivate under harsh reaction conditions. In this study, we introduce a novel heterogeneous catalyst for the Ullmann-type C−O coupling reaction, comprised of isolated Cu atoms chelated to a tetraethylenepentamine-pyrrole ligand that is immobilized on graphite nanoplatelets. The catalytic study reveals the recyclability of the material, and demonstrates the crucial role of the pyrrole linker in stabilizing the Cu sites. The work expands the potential of single-atom catalyst nanoarchitectures and underscores the significance of ligands in stabilizing metals in cationic forms, providing a novel, tailored catalyst for cross-coupling chemistries.

Copper Single Atoms Chelated on Ligand-Modified Carbon for Ullmann-type C−O Coupling

Ruta V.;Moriggi F.;Bussetti G.;Barbera V.;Bajada M. A.;Galimberti M.;Vile G.
2024-01-01

Abstract

Cross-coupling reactions are of great importance in chemistry due to their ability to facilitate the construction of complex organic molecules. Among these reactions, the Ullmann-type C−O coupling between phenols and aryl halides is particularly noteworthy and useful for preparing diarylethers. However, this reaction typically relies on homogeneous catalysts that rapidly deactivate under harsh reaction conditions. In this study, we introduce a novel heterogeneous catalyst for the Ullmann-type C−O coupling reaction, comprised of isolated Cu atoms chelated to a tetraethylenepentamine-pyrrole ligand that is immobilized on graphite nanoplatelets. The catalytic study reveals the recyclability of the material, and demonstrates the crucial role of the pyrrole linker in stabilizing the Cu sites. The work expands the potential of single-atom catalyst nanoarchitectures and underscores the significance of ligands in stabilizing metals in cationic forms, providing a novel, tailored catalyst for cross-coupling chemistries.
2024
covalent adducts
cross-coupling chemistry
functional carbon materials
graphite nanoplatelets
single-atom catalysis
File in questo prodotto:
File Dimensione Formato  
ChemSusChem - 2023 - Ruta - Copper Single Atoms Chelated on Ligand‐Modified Carbon for Ullmann‐type C O Coupling (1).pdf

accesso aperto

: Publisher’s version
Dimensione 4.51 MB
Formato Adobe PDF
4.51 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11311/1264415
Citazioni
  • ???jsp.display-item.citation.pmc??? 0
  • Scopus 0
  • ???jsp.display-item.citation.isi??? ND
social impact