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

Five novel benzimidazole salts (\textbf{1}--\textbf{5}) having N-phthalimidoethyl and 4-substituted benzyl were synthesized and identified by $^{1}$H NMR, $^{13}$C NMR, and IR spectroscopic methods and microanalysis. A mixture of the benzimidazole salts (\textbf{1}--\textbf{5}), Pd(OAc)$_{2}$, and K$_{2}$CO$_{3}$ in DMF-H$_{2}$O 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 (\textbf{1}--\textbf{5}), Pd(OAc)$_{2}$, Cs$_{2}$CO$_{3}$, PEG, and Cu nanoparticles catalyzed, in high yield, the Sonogashira coupling reaction promoted by microwave irradiation in 10 min. The same benzimidazole salts (\textbf{1}--\textbf{5}), Pd(OAc)$_{2}$, Cs$_{2}$CO$_{3}$, 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.

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

Five novel benzimidazole salts (\textbf{1}--\textbf{5}) having N-phthalimidoethyl and 4-substituted benzyl were synthesized and identified by $^{1}$H NMR, $^{13}$C NMR, and IR spectroscopic methods and microanalysis. A mixture of the benzimidazole salts (\textbf{1}--\textbf{5}), Pd(OAc)$_{2}$, and K$_{2}$CO$_{3}$ in DMF-H$_{2}$O 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 (\textbf{1}--\textbf{5}), Pd(OAc)$_{2}$, Cs$_{2}$CO$_{3}$, PEG, and Cu nanoparticles catalyzed, in high yield, the Sonogashira coupling reaction promoted by microwave irradiation in 10 min. The same benzimidazole salts (\textbf{1}--\textbf{5}), Pd(OAc)$_{2}$, Cs$_{2}$CO$_{3}$, 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.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

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Copper-free Sonogashira cross-coupling reactions catalyzed by an efficient dimericC,N-palladacycle in DMF/H2O

Kazem KARAMI, Nasrin HAGHIGHAT NAEINI

Monodisperse palladium nanoparticles supported on chemically derived graphene: highly active and reusable nanocatalysts for Suzuki{Miyaura cross-coupling reactions

Feyyaz DURAP, Önder METİN

Contribution of heterobifunctional ligands to transition metal-catalysed C--C coupling reactions

Agnes LABANDE, Eric DEYDIER, Eric MANOURY, Jean-claude DARAN, Catherine AUDIN, Rinaldo POLI

Reactivity of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1$H)$-ones in a palladium catalyzed Sonogashira cross-coupling reaction

Malose Jack MPHAHLELE, Felix Adetunji OYEYIOLA

Substituted 2-(2''-pyridyl)benzimidazole palladium(II) complexes as an efficient catalytic system for Suzuki--Miyaura cross-coupling reactions

MAHMUT ULUSOY, NURDAL ÖNCEL, Emine AYTAR

Palladium-catalysed Suzuki{Miyaura cross-coupling with imidazolylidene ligandssubstituted by crowded resorcinarenyl and calixarenyl units

Neslihan ŞAHİN, Dominique MATT, David SEMERIL, Eric BRENNER, Loic TOUPET, Cemal KAYA

Substituted 2-(2'-pyridyl)benzimidazole palladium(II) complexes as an efficient catalytic system for Suzuki{Miyaura cross-coupling reactions

Mahmut ULUSOY, Nurdal ÖNCEL, Emine AYTAR