Thiazoline-Iridium (III) Complexes and Immobilized Nanomaterials as Selective Catalysts inN-Alkylation of Amines with Alcohols

DENİZALTI S., DAYAN S., GÜNNAZ S., ŞAHİN E.

APPLIED ORGANOMETALLIC CHEMISTRY, cilt.34, sa.12, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 34 Sayı: 12
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1002/aoc.5970
  • Dergi Adı: APPLIED ORGANOMETALLIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, BIOSIS, Chimica, Communication Abstracts, Compendex, Metadex, DIALNET, Civil Engineering Abstracts
  • Anahtar Kelimeler: alkylation of amine, GO, iridium complex, MWCNT, nanomaterial, N-HETEROCYCLIC CARBENE, AROMATIC-AMINES, HETEROGENEOUS CATALYSIS, EFFICIENT NANOCATALYST, TRANSFER HYDROGENATION, SECONDARY ALCOHOLS, OXIDATION, DESFERRITHIOCIN, METHYLATION, ACTIVATION
  • Erciyes Üniversitesi Adresli: Evet

Özet

In this research, a new series of thiazoline-iridium (III) complexes (4-7) derived from cysteine were prepared and fully characterized by conventional methods. The molecular structure of complex5was also determined by single-crystal X-ray diffraction. These complexes were evaluated as catalysts for hydrogen-borrowing reactions of amines with alcohols. In particular, complex5showed the best activity as catalyst. Various amines have been alkylated with alcohols affording moderate to good yield (33-99%). Moreover, the immobilized nanomaterials (M-1,M-2) were fabricated by sonication process from the best catalyst5with the multi-walled carbon nanotubes (MWCNTs) and graphene oxide (GO), respectively, and characterized by X-ray diffraction (XRD), Fourier transform infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray (EDX) spectroscopy, and inductively coupled plasma-mass spectrometry (ICP-MS). TheM(1,2)nanomaterials were also tested as catalysts in model catalytic reaction forN-alkylation. TheM(1)nanomaterial showed significantly higher activity than theM(2)nanomaterial. TheM(1)catalyst was recovered by filtration and reused for four catalytic cycles with high conversion (99%, 97%, 96%, and 86%).