Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald-Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties

KÜÇÜKBAY H., Yilmaz U., YAVUZ K., BUGDAY N.

TURKISH JOURNAL OF CHEMISTRY, cilt.39, sa.6, ss.1265-1290, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 39 Sayı: 6
  • Basım Tarihi: 2015
  • Doi Numarası: 10.3906/kim-1505-34
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.1265-1290
  • Anahtar Kelimeler: Heck-Mizoroki coupling, Suzuki-Miyaura coupling, Sonogashira coupling, Buchwald-Hartwig coupling, benzimidazole derivatives, catalyzes, N-heterocyclic carbene, microwave, C-C, PALLADIUM COMPLEXES, PD NANOPARTICLES, ARYL CHLORIDES, MIZOROKI-HECK, MIYAURA, COPPER, HALIDES, SUBSTITUENTS, HETEROCYCLES
  • İnönü Üniversitesi Adresli: Evet

Özet

Five novel benzimidazole salts (1-5) having N-phthalimidoethyl and 4-substituted benzyl were synthesized and identified by H-1 NMR, C-13 NMR, and IR spectroscopic methods and microanalysis. A mixture of the benzimidazole salts (1-5), Pd(OAc)(2), and K2CO3 in DMF-H2O catalyzed, in high yield, the Suzuki-Miyaura and the Heck-Mizoroki cross-coupling reactions assisted by microwave irradiation in 5 min. The novel benzimidazole salts (1-5), Pd(OAC)(2), CS2CO3, PEG, and Cu nanoparticles catalyzed, in high yield, the Sonogashira coupling reaction promoted by microwave irradiation in 10 min. The same benzimidazole salts (1-5), Pd(OAc)(2), CS2CO3, and TBAB catalyzed, in moderate or low yield, the Buchwald-Hartwig reaction assisted by microwave irradiation in 60 min. The efficiency of the catalyst system in these four reactions was discussed as well as the electron-releasing and withdrawing substituent effects on the benzimidazole ligands.