Palladium-carbene catalyzed direct arylation of five-membered heteroaromatics

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

JOURNAL OF MOLECULAR STRUCTURE, cilt.1206, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1206
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.molstruc.2019.127668
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Compendex, INSPEC
  • Anahtar Kelimeler: N-Heterocyclic carbene, Palladium, PEPPSI, Direct arylation, Heteroaromatics, N-HETEROCYCLIC CARBENE, CROSS-COUPLING REACTIONS, C-H BOND, PD-NHC PRECATALYST, PEPPSI COMPLEXES, ARYL BROMIDES, ROOM-TEMPERATURE, BENZIMIDAZOLIUM SALTS, FUNCTIONALIZATION, REACTIVITY
  • İnönü Üniversitesi Adresli: Evet

Özet

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.