Synthesis, characterization and catalytic activity of PEPPSI-type palladium-NHC complexes

Slimani I., Mansour L., ÖZDEMİR İ., GÜRBÜZ N., Hamdi N.

INORGANICA CHIMICA ACTA, cilt.515, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 515
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1016/j.ica.2020.120043
  • Dergi Adı: INORGANICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core
  • Anahtar Kelimeler: N-Heterocyclic carbene, PEPPSI-type palladium-NHC complexes, Benzimidazolium salts, Direct arylation, HETEROCYCLIC CARBENE COMPLEXES, CROSS-COUPLING REACTIONS, SUZUKI-MIYAURA, PD-PEPPSI, ROOM-TEMPERATURE, PRECATALYST, ARYLATION, LIGANDS, EFFICIENT, CHLOROPYRAZINES
  • İnönü Üniversitesi Adresli: Evet

Özet

Eight benzimidazolium salts (2a-h) with two nitrogen atoms substituted by various alkyl groups have been synthesized in high yields. The benzimidazolium salts were readily converted into the corresponding PEPPSItype palladium-NHC complexes (PEPPSI = pyridine-enhanced precatalyst preparation, stabilization, and initiation) (3a-h). The structures of all compounds were characterized by H-1 NMR, C-13 NMR, and IR spectroscopy as well as by elemental analysis techniques, which support the proposed structures. The catalytic activity of the PEPPSI-type palladium-NHC complexes was evaluated with respect to the direct C5-arylation of 2-substituted heteroaryl derivatives (thiophene, furan and thiazole) with various aryl bromides. This arylation occurs efficiently and selectively at the C5-position of the 2-substituted thiophene, furan and thiazole derivatives.