Palladium(ii)/N-heterocyclic carbene (NHC) catalyzed direct C-H arylation of heteroarenes with different aryl bromides and chlorides - Université de Lille Accéder directement au contenu
Article Dans Une Revue New Journal of Chemistry Année : 2023

Palladium(ii)/N-heterocyclic carbene (NHC) catalyzed direct C-H arylation of heteroarenes with different aryl bromides and chlorides

D. Bensalah
  • Fonction : Auteur
L. Mansour
  • Fonction : Auteur
N. Gurbuz
  • Fonction : Auteur
I. Ozdemir
  • Fonction : Auteur
W. S. Koko
  • Fonction : Auteur
R. Gatri
  • Fonction : Auteur
N. Hamdi
  • Fonction : Auteur

Résumé

The growing interest of industry in the field of bi(hetero)arene compounds motivated us to synthesize these compounds via a homogeneous catalytic route using Pd PEPPSI-type complexes through direct arylation. In this study, new Pd PEPPSI-type complexes bearing NHC spectator ligands were synthesized and characterized using spectroscopic techniques, such as 1HNMR, 13C NMR, MS spectrometry, FTIR spectroscopy and elemental analysis (PEPPSI = pyridine enhanced precatalyst preparation stabilization and initiation). All the synthesized Pd(II) complexes were stable. The catalytic properties of these complexes were evaluated in the direct C5 mono-arylation of furan, 2-acetylthiophene and N-methylpyrrole-2-carboxaldehyde derivatives with a wide variety of (hetero)aryl halides. This environmentally attractive procedure was found to be tolerant of a wide variety of functional groups on the aryl halides and good yields were obtained in the presence of 1 mol% catalyst loading at 150 °C for 2 hours. In addition, the conversions for substrates containing electron-withdrawing groups were higher than those for substituents containing electron-donating groups.

Domaines

Chimie
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Dates et versions

hal-04547735 , version 1 (16-04-2024)

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Citer

D. Bensalah, L. Mansour, Mathieu Sauthier, N. Gurbuz, I. Ozdemir, et al.. Palladium(ii)/N-heterocyclic carbene (NHC) catalyzed direct C-H arylation of heteroarenes with different aryl bromides and chlorides. New Journal of Chemistry, 2023, New Journal of Chemistry, 47, ⟨10.1039/d3nj04209j⟩. ⟨hal-04547735⟩
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