Arylation of heterocyclic compounds by benzimidazole-based N-heterocyclic carbene-palladium(II) complexes

ŞAHİN N., GÜRBÜZ N., KARABIYIK H., KARABIYIK H., ÖZDEMİR İ.

JOURNAL OF ORGANOMETALLIC CHEMISTRY, cilt.907, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 907
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.jorganchem.2019.121076
  • Dergi Adı: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Compendex
  • Anahtar Kelimeler: N-heterocyclic carbene, Benzimidazole, PEPPSI, Direct arylation, Thiophenes, Thiazoles, METALATION-DEPROTONATION MECHANISM, CATALYZED DIRECT ARYLATION, CROSS-COUPLING REACTIONS, PALLADIUM COMPLEXES, CARBENE COMPLEXES, ARYL BROMIDES, PD, NHC, THIOPHENE, CHLOROPYRAZINES
  • İnönü Üniversitesi Adresli: Evet

Özet

Specific C-H bond can be activated for arylation using aryl halide without the aid of directing the group in the case of electron-rich heteroarenes. The ability to readily generate halo substituted arylated heteroarenes is important in organic chemistry since these species are important building blocks for biochemists. In this manuscript, we report the synthesis of PEPPSI type-novel benzimidazole-based N-heterocyclic carbene-palladium(II) complexes (2a-e). All of the new compounds were fully characterized by H-1, C-13{H-1} NMR and FT-IR spectra. The structures of 2c, 2d, and 2e were determined by X-ray crystallography and the prepared complexes (2a-e) were investigated as catalysts for the direct arylation of 2-n-propylthiazole, 4,5-dimethylthiazole and 2-acetylthiophene with various aryl bromides. High catalytic activity for arylation was seen reaction using only 0.5 mol% catalyst for 1 h. (C) 2019 Elsevier B.V. All rights reserved.