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    Palladium(II) N-heterocyclic carbene complexes as catalysts for the direct arylation of pyrrole derivatives with aryl chlorides
    (Elsevier Science Sa, 2017) Yigit, Beyhan; Gurbuz, Nevin; Yigit, Murat; Dagdeviren, Zeynep; Ozdemir, Ismail
    Silver(I) N-heterocyclic carbene complexes were synthesized in good yields by the reactions of 1,3-dialkylperhydrobenzimidazolyum salts with silver(I) oxide and used as transmetallation reagents for the synthesis of palladium(II) N-heterocyclic carbene complexes. All of the complexes were characterized using elemental analysis, H-1 NMR and C-13 NMR spectroscopy. The catalytic activity of Pd(II)-NHC complexes in the direct arylation of pyrrole derivatives was investigated. These Pd(II)-NHC complexes showed the good catalytic performance for the direct arylation of pyrrole derivatives with readily available and inexpensive aryl chlorides. The arylation reactions regioselectively produced C2- or C5-arylation products in moderate to good yields by using 1 mol% of the palladium complex. (C) 2017 Elsevier B.V. All rights reserved.
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    Synthesis of silver(I) and palladium(II) N-heterocyclic carbene complexes and their use as catalysts for the direct C5 arylation of heteroaromatic compounds
    (Springer, 2016) Yigit, Beyhan; Yigit, Murat; Dagdeviren, Zeynep; Ozdemir, Ismail
    Silver(I) N-heterocyclic carbene complexes were synthesized in good yields by the reactions of 1,3-dialkylperhydrobenzimidazolium salts with silver(I) oxide in dichloromethane. The silver complexes were used as carbene-transfer agents to synthesize palladium(II) N-heterocyclic carbene complexes. All of the complexes were characterized by physicochemical and spectroscopic methods. The new palladium complexes were tested as catalysts in the direct C5 arylation of 2-n-butylfuran, 2-n-butylthiophene and 2-n-propylthiazole with aryl bromides at 130 A degrees C in N,N-dimethylacetamide. The arylation reactions proceeded selectively at the C5 position of the heteroaromatic compounds, and the corresponding coupling products were obtained in moderate to good yields by using 0.5 mol% of the palladium complex.