Palladium-carbene catalyzed direct arylation of five-membered heteroaromatics

KALOĞLU M. , Kaloglu N., Ylidirim I., ÖZDEMİR N., ÖZDEMİR İ.

JOURNAL OF MOLECULAR STRUCTURE, vol.1206, 2020 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1206
  • Publication Date: 2020
  • Doi Number: 10.1016/j.molstruc.2019.127668


Due to the industrial importance of bi(hetero)arenes, the synthesis of these compounds by homogeneous Pd-catalyzed direct arylation is an important research topic in modern organic chemistry. In this study, PEPPSI-type, (PEPPSI = Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation), new Pd-catalysts with N-heterocyclic carbene ligand were synthesized, and they were used as catalysts in the synthesis of bi(hetero)arenes by direct arylation process. The structures of Pd-carbene complexes were elucidated by different spectroscopic and analytical techniques such as NMR, FT-IR and elemental analysis. The more detailed structural characterization of one of the complexes was determined by single-crystal X-ray diffraction study. Pd-carbene complexes were used as effective catalysts in the direct arylation of five-membered heteroaromatics such as thiophene, furan and thiazole derivatives with (hetero)aryl bromides for 1 h, in the presence of 1 mol% of catalyst loading, and successful results were obtained. (C) 2020 Elsevier B.V. All rights reserved.