Imidazol-2-ylidene-Pd-PEPPSI complexes containing 4-acetylphenyl side arm: Synthesis, characterization, crystal structure, and applications in Suzuki, Heck and Sonogashira reactions


Demirci Ö., BARUT CELEPCİ D., GÖK Y., AKTAŞ A., AYGÜN M.

Inorganica Chimica Acta, vol.588, 2025 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 588
  • Publication Date: 2025
  • Doi Number: 10.1016/j.ica.2025.122845
  • Journal Name: Inorganica Chimica Acta
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex
  • Keywords: Crystal structure, Imidazole, PEPPSI, Suzuki-Miyaura, Mizoroki-heck, Sonogashira
  • Dokuz Eylül University Affiliated: Yes

Abstract

This study presents the synthesis of new Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation (PEPPSI) type N-heterocyclic carbene (NHC)-Pd(II) complexes featuring a 4-acetylphenyl side arm, which demonstrate stability in the presence of air and moisture and function as homogeneous catalysts. All complexes were characterized using the elemental analysis technique and FTIR, 1H NMR, and 13C NMR spectroscopic methods. In addition, the molecular and crystal structures of the five complexes (2a, 2c, 2d, 2e, 2g) were determined by single crystal X-ray diffraction (SC-XRD). These complexes have been investigated for their catalytic abilities in the Suzuki-Miyaura cross-coupling reactions of aryl chlorides and bromides with aryl boronic acid derivatives, the Heck cross-coupling reactions of aryl bromides with styrene, and the cross-coupling reactions of aryl bromides with phenylacetylene. In addition, we investigated the catalytic activities of some complexes (2e, 2g) in the Sonogashira coupling reaction. The catalytic activities of these homogeneous catalysts in C[sbnd]C coupling reactions were determined by varying various parameters such as solvent, base, temperature and time. They were found to be active catalysts under these conditions.