The direct C4-arylation of 3,5-dimethylisoxazole with aryl bromides catalyzed by imidazolidin-2-ylidene based palladium-PEPPSI complexes

KALOĞLU M., ÖZDEMİR İ.

INORGANICA CHIMICA ACTA, cilt.504, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 504
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.ica.2020.119454
  • Dergi Adı: INORGANICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica
  • Anahtar Kelimeler: N-heterocyclic carbene, Imidazolidin-2-ylidene, Palladium, PEPPSI, Direct arylation, Isoxazole, N-HETEROCYCLIC CARBENES, DIRECT ARYLATION, CONVENIENT SYNTHESIS, METAL-COMPLEXES, IMIDAZOLIDINIUM, DERIVATIVES, VALDECOXIB, ISOXAZOLES, CHEMISTRY, OXAZOLES
  • İnönü Üniversitesi Adresli: Evet

Özet

In this study, the synthesis and characterization of four new imidazolinium salts as carbene precursors and their corresponding four new PEPPSI-type (PEPPSI = Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation) palladium complexes were reported. The structures of these new compounds were characterized by spectroscopic and analytical techniques. The catalytic activities of all palladium complexes were evaluated in the direct C4-arylation of 3,5-dimethylisoxazole with para-substituted aryl bromides, ortho-substituted aryl bromides and heteroaryl bromides. A range of functional groups such as methoxy, acetyl, formyl, fluoro, trifluoromethyl, nitrile or tert-butyl on the aryl bromide were succesfully tolerated, and good yields were generally obtained in presence of 1 mol% catalyst loading at 120 degrees C.