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

Authors

ÜLKÜ YILMAZ
HASAN KÜÇÜKBAY

Abstract

Many benzimidazole salts bearing a 3-phenylpropyl substituent (1a-1h) were synthesized and their structures were identified by $^{1}$H NMR, $^{13}$C 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.

DOI

10.3906/kim-1804-39

Keywords

Benzimidazole salt, NHC precursor, catalyst, Suzuki--Miyaura reaction, cyclotrimerization of phenyl isocyanate

First Page

1706

Last Page

1719

Recommended Citation

YILMAZ, ÜLKÜ and KÜÇÜKBAY, HASAN (2018) "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," Turkish Journal of Chemistry: Vol. 42: No. 6, Article 19. https://doi.org/10.3906/kim-1804-39
Available at: https://journals.tubitak.gov.tr/chem/vol42/iss6/19