Ruthenium(II)-(p-cymene)-N-Heterocyclic Carbene Complexes for the N-Alkylation of Amine Using the Green Hydrogen Borrowing Methodology

KALOĞLU M., GÜRBÜZ N., SEMERIL D., ÖZDEMİR İ.

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, sa.10, ss.1236-1243, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: Sayı: 10
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1002/ejic.201701479
  • Dergi Adı: EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1236-1243
  • Anahtar Kelimeler: N-Heterocyclic carbenes, Ruthenium, Amines, N-Alkylation, Hydrogen borrowing strategy, RUTHENIUM-CATALYZED AMINATION, HETEROCYCLIC CARBENE, SECONDARY ALCOHOLS, METATHESIS CATALYSTS, SELECTIVE ALKYLATION, ALKENE METATHESIS, LIGAND PRECURSORS, IRIDIUM COMPLEX, BETA-ALKYLATION, AROMATIC AMINE
  • İnönü Üniversitesi Adresli: Evet

Özet

Six ruthenium(II) complexes with the general molecular formula [RuCl2(NHC)((6)-p-cymene)] (NHC = N-heterocyclic carbene) were synthesized by the transmetalation method from [RuCl2((6)-p-cymene)](2) and silver(I)-NHC complexes. All complexes were fully characterized by analytical and spectral methods (FT-IR, elemental analysis and H-1 and C-13 NMR). The solid-state structure of one of the ruthenium complexes [dichloro-{1-[2-(2-ethoxyphenoxy)ethyl]-3-(3,5-dimethylbenzyl)benzimidazol-2-ylidene}(p-cymene) ruthenium(II)] has been established by single-crystal X-ray diffraction study, which revealed that the ruthenium atom adopt a classical piano-stool coordination geometry. Under the optimised conditions, these ruthenium complexes were found to be efficient catalysts for N-alkylation of aniline with arylmethyl alcohols using the hydrogen borrowing strategy, which is a cost-effective and environmentally attractive reaction for the preparation of N-alkylated amines.