Synthesis of novel benzimidazole salts and microwave-assisted catalytic activity of in situ generated Pd nanoparticles from a catalyst system consisting of benzimidazol salt, Pd(OAc)_2, and base in a Suzuki-Miyaura reaction

Authors

ÜLKÜ YILMAZ
HASAN KÜÇÜKBAY
SEVİM TÜRKTEKİN ÇELİKESİR
MEHMET AKKURT
ORHAN BÜYÜKGÜNGÖR

DOI

10.3906/kim-1207-18

Abstract

Novel benzimidazolium salts having N-benzyl or N-(4-substitutedbenzyl) groups were synthesized and their microwave-promoted catalytic activity for the Suzuki--Miyaura cross-coupling reaction were determined using in situ formed palladium(0) nanoparticles (PdNPs) from a catalytic system consisting of Pd(OAc)_2/K2CO_3 in DMF/H_2O. PdNPs were characterized by X-ray diffraction (XRD) pattern and particle size of in situ generated PdNPs from the Pd(111) plane was determined to be of diameter 19.6 nm by the Debye--Scherrer equation. Moreover, the yield of the Suzuki--Miyaura reactions with aryl iodides and aryl bromides was found to be nearly quantitative. The synthesized benzimidazole salts (1--5) were identified by ^1H and ^{13}C NMR and IR spectroscopic methods, and micro analysis. The molecular structure of 5 was also determined by X-ray crystallography.

Keywords

Benzimidazole salt, N-heterocyclic carbenes, palladium nanoparticles, cross-coupling reaction, Suzuki--Miyaura coupling, microwave

First Page

721

Last Page

733

Recommended Citation

YILMAZ, ÜLKÜ; KÜÇÜKBAY, HASAN; ÇELİKESİR, SEVİM TÜRKTEKİN; AKKURT, MEHMET; and BÜYÜKGÜNGÖR, ORHAN (2013) "Synthesis of novel benzimidazole salts and microwave-assisted catalytic activity of in situ generated Pd nanoparticles from a catalyst system consisting of benzimidazol salt, Pd(OAc)_2, and base in a Suzuki-Miyaura reaction," Turkish Journal of Chemistry: Vol. 37: No. 5, Article 3. https://doi.org/10.3906/kim-1207-18
Available at: https://journals.tubitak.gov.tr/chem/vol37/iss5/3