The catalytic effects of in situ prepared N-heterocyclic carbenes from benzimidazole salts in Suzuki-Miyaura cross-coupling reaction and uses in catalytic preparation of 1,3,5-triphenyl-1,3,5-triazinane-2,4,6-trione from phenyl isocyanate

Yilmaz U., KÜÇÜKBAY H.

TURKISH JOURNAL OF CHEMISTRY, cilt.42, sa.6, ss.1706-1736, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 42 Sayı: 6
  • Basım Tarihi: 2018
  • Doi Numarası: 10.3906/kim-1804-39
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.1706-1736
  • Anahtar Kelimeler: Benzimidazole salt, NHC precursor, catalyst, Suzuki-Miyaura reaction, cyclotrimerization of phenyl isocyanate, ELECTRON-RICH OLEFINS, SUBSTITUTED BENZIMIDAZOLE, CRYSTAL-STRUCTURES, HECK-MIZOROKI, CYCLOTRIMERIZATION, COMPLEXES, TRIMERIZATION, WATER, ISOCYANURATE, ORGANOCATALYSTS
  • İnönü Üniversitesi Adresli: Evet

Özet

Many benzimidazole salts bearing a 3-phenylpropyl substituent (1a-1h) were synthesized and their structures were identified by H-1 NMR, C-13 NMR, and IR spectroscopic methods and elemental analysis. These N-heterocyclic carbene (NHC) precursors were used as a part of a catalytic system including Pd(OAc)(2) and the base in the Suzuki-Miyaura cross-coupling reaction under microwave irradiation. They were also used as catalysts in the cyclotrimerization of phenyl isocyanate to yield 1,3,5-triphenyl-1,3,5-triazinane-2,4,6-trione. It has been observed that benzimidazole salts made a positive contribution to both catalytic reactions as a NHC precursor.