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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

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Abstract

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 °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.

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Acknowledgments

We thank the Adıyaman University Research Fund (FEFMAP/2015-0004) for financial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science and Art, Adıyaman University, 02040, Adıyaman, Turkey

    Beyhan Yiğit, Murat Yiğit & Zeynep Dağdeviren

  2. Department of Chemistry, Faculty of Science and Art, Inönü University, 44260, Malatya, Turkey

    İsmail Özdemir

Authors
  1. Beyhan Yiğit
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  2. Murat Yiğit
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  3. Zeynep Dağdeviren
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  4. İsmail Özdemir
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Correspondence to Murat Yiğit.

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Yiğit, B., Yiğit, M., Dağdeviren, Z. et al. Synthesis of silver(I) and palladium(II) N-heterocyclic carbene complexes and their use as catalysts for the direct C5 arylation of heteroaromatic compounds. Transit Met Chem 41, 751–757 (2016). https://doi.org/10.1007/s11243-016-0075-y

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  • DOI: https://doi.org/10.1007/s11243-016-0075-y

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