Ruthenium(n6,n1-arene-CH2-NHC) Catalysts for Direct Arylation of 2-Phenylpyridine with (Hetero)Aryl Chlorides in Water

KALOGLU N., ÖZDEMİR İ., GÜRBÜZ N., Arslan H., DIXNEUF P. H.

MOLECULES, cilt.23, sa.3, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 23 Sayı: 3
  • Basım Tarihi: 2018
  • Doi Numarası: 10.3390/molecules23030647
  • Dergi Adı: MOLECULES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Anahtar Kelimeler: homogeneous catalysis, ruthenium, N-heterocyclic carbene, 2-phenylpyridine, direct arylation, single crystal structure, CROSS-COUPLING REACTIONS, C-H BONDS, ARYL CHLORIDES, COMPLEXES, ACTIVATION, FUNCTIONALIZATION, HALIDES, ARENES, RUTHENIUM(II), DERIVATIVES
  • İnönü Üniversitesi Adresli: Evet

Özet

A series of new benzimidazolium halides were synthesized in good yields as unsymmetrical N-heterocyclic carbene (NHC) precursors containing the N-CH2-arene group. The benzimidazolium halides were readily converted into ruthenium(II)-NHC complexes with the general formula [RuCl2 (eta(6),eta(1)-arene-CH2-NHC)]. The structures of all new compounds were characterized by H-1 NMR (Nuclear Magnetic Resonance), C-13 NMR, FT-IR (Fourier Transform Infrared) spectroscopy and elemental analysis techniques. The single crystal structure of one benzimidazole ruthenium complex, 2b, was determined. The complex is best thought of as containing an octahedrally coordinated Ru center with the arene residue occupying three sites, the remaining sites being occupied by a (carbene)C-Ru bond and two Ru-Cl bonds. The catalytic activity of [RuCl2(eta(6),eta(1)-arene-CH2 -NHC)] complexes was evaluated in the direct (hetero)arylation of 2-phenylpyridine with (hetero)aryl chlorides in water as the nontoxic reaction medium. These results show that catalysts 2a and 2b were the best for monoarylation with simple phenyl and tolyl chlorides. For functional aryl chlorides, 2d, 2e, and 2c appeared to be the most efficient.