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Catalytic activities in direct arylation of novel palladium N ‐heterocyclic carbene complexes
Author(s) -
Akkoç Senem,
Gök Yetkin
Publication year - 2014
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3220
Subject(s) - chemistry , carbene , palladium , benzonitrile , catalysis , dichloromethane , medicinal chemistry , aryl , proton nmr , stereochemistry , organic chemistry , solvent , alkyl
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, 1 H NMR and 13 C 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°C for 1 h. The complexes showed very good catalytic activities in these reactions. Copyright © 2014 John Wiley & Sons, Ltd.