Bioactive NHC-derived palladium complexes: synthesis, catalytic activity for the Suzuki-Miyaura coupling of aryl chlorides and bromides and their antibacterial activities


Boubakri L., Al-Ayed A. S. , Mansour L., Abutaha N., Harrath A. H. , Ozdemir I., ...Daha Fazla

JOURNAL OF COORDINATION CHEMISTRY, cilt.72, ss.2688-2704, 2019 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 72 Konu: 16
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1080/00958972.2019.1664738
  • Dergi Adı: JOURNAL OF COORDINATION CHEMISTRY
  • Sayfa Sayıları: ss.2688-2704

Özet

Pd(II)-bis(NHC) complexes (where NHC = N-heterocyclic carbene) bearing asymmetrically and symmetrically substituted NHC-ligand have been synthesized via deprotonation of 5,6-dimethylbenzimidazolium salts. The NHC precursors have been achieved via the two step N-alkylation of 5,6-dimethylbenzimidazole. The resultant salts were deprotonated with PdCl2 and K2CO3 in dry THF for 2(a-e). The obtained complexes were identified and characterized by H-1 and C-13 NMR, FT-IR, DART-TOF mass spectrometry and elemental analysis. These new Pd(II)-bis(NHC) complexes were applied as catalyst precursors for Suzuki-Miyaura cross-coupling reactions of aryl bromides and chlorides with phenylboronic acid to afford the corresponding products in good yields. This catalytic reaction was evaluated in the presence of KOtBu/toluene. The antibacterial activities of 2(a-e) were investigated against Gram (+)/(-) bacteria using the agar dilution procedure. The antibacterial activities of 2 vary with the nature of the ligands; MIC values of 2(a-e) were determined.