Catalytic activities in direct arylation of novel palladium N-heterocyclic carbene complexes


Akkoc S. , GÖK Y.

APPLIED ORGANOMETALLIC CHEMISTRY, vol.28, no.12, pp.854-860, 2014 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 28 Issue: 12
  • Publication Date: 2014
  • Doi Number: 10.1002/aoc.3220
  • Title of Journal : APPLIED ORGANOMETALLIC CHEMISTRY
  • Page Numbers: pp.854-860

Abstract

Eight novel palladium N-heterocyclic carbene (Pd-NHC) complexes were synthesized by the reaction of chloro 1,3-dialkylbenzimidazolin-2-ylidene silver(I) complexes with bis(benzonitrile)palladium(II) chloride in dichloromethane. These eight Pd-NHC complexes are as follows: bis[1-phenyl-3-(2,4,6-trimethylbenzyl)benzimidazol-2-ylidene]dichloropalladium(II), bis[1-phenyl-3-(2,3,5,6-tetramethylbenzyl)benzimidazol-2-ylidene]dichloropalladium(II), bis[1-phenyl-3-(2,3,4,5,6-pentamethylbenzyl)benzimidazol-2-ylidene]dichloropalladium(II), bis[1-phenyl-3-(3,4,5-trimethoxybenzyl)benzimidazol-2-ylidene]dichloropalladium(II), bis[1-(2-diethylaminoethyl)-3-(3-methylbenzyl)benzimidazol-2-ylidene]dichloropalladium(II), bis[1-(2-diethylaminoethyl)-3-(2,3,5,6-tetramethylbenzyl)benzimidazol-2-ylidene]dichloropalladium(II),bis[1-(2-morpholinoethyl)-3-naphthalenomethylbenzimidazol-2-ylidene]dichloropalladium(II) and bis[1-(2-morpholinoethyl)-3-(2-methylbenzyl)benzimidazol-2-ylidene]dichloropalladium(II). Also, these synthesized complexes were fully characterized using Fourier transform infrared, H-1 NMR and C-13 NMR spectroscopic methods and elemental analysis techniques. These synthesized novel Pd-NHC complexes were tested as catalysts in the direct arylation of 2-n-butylthiophene, 2-n-butylfuran and 2-isopropylthiazole with various aryl bromides at 130 degrees C for 1 h. The complexes showed very good catalytic activities in these reactions. Copyright (c) 2014 John Wiley & Sons, Ltd.