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Palladium(II) Complexes with Benzimidazolin-2-ylidene and Phosphane Ligands and their Catalytic Activity in Mizoroki–Heck Coupling Reactions

  1. Hayati Türkmen1,
  2. Tania Pape2,
  3. F. Ekkehardt Hahn2,
  4. Bekir Çetinkaya1

Article first published online: 4 DEC 2008

DOI: 10.1002/ejic.200800948

Issue

European Journal of Inorganic Chemistry

European Journal of Inorganic Chemistry

Volume 2009, Issue 2, pages 285–294, January 2009

Additional Information

How to Cite

Türkmen, H., Pape, T., Hahn, F. E. and Çetinkaya, B. (2009), Palladium(II) Complexes with Benzimidazolin-2-ylidene and Phosphane Ligands and their Catalytic Activity in Mizoroki–Heck Coupling Reactions. Eur. J. Inorg. Chem., 2009: 285–294. doi: 10.1002/ejic.200800948

Author Information

  1. 1

    Department of Chemistry, Ege University, 35100 Bornova-Izmir, Turkey, Fax: +90-232-3888264

  2. 2

    Institut für Anorganische und Analytische Chemie, Westfälische Wilhelms-Universität Münster, Corrensstraße 36, 48149 Münster, Germany, Fax: +49-251-8333108

Publication History

  1. Issue published online: 29 DEC 2008
  2. Article first published online: 4 DEC 2008
  3. Manuscript Received: 25 SEP 2008

Funded by

  • Ege University
  • University of Münster
  • Deutsche Forschungsgemeinschaft
  • Fonds der Chemischen Industrie

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Keywords:

  • N ligands;
  • Phosphanes;
  • Palladium;
  • Carbene ligands;
  • Cross-coupling

Abstract

Symmetrically and unsymmetrically substituted benzimidazolium bromides (1a–d = NHC·HBr) were synthesized, incorporating bulky benzyl and/or methoxyethyl substituents (a: R = pentamethylbenzyl, R′ = 2-methoxyethyl; b: R = 2,3,5,6-tetramethylbenzyl, R′ = methoxyethyl; c: R, R′ = pentamethylbenzyl; d: R, R′ = 2,3,5,6-tetramethylbenzyl). The salts were used to prepare NHC palladium complexes. Reaction of 1a–d with Pd(OAc)2 and NaBr in a 1:1:3 ratio in dmso gave mono or dinuclear, bromide-bridged complexes of type 2. Complexes of type 2 react with monodentate or bidentate phosphanes in CH2Cl2 to afford the mixed benzimidazolin-2-ylidene-phosphane complexes 3–6. Reaction of salts 1a–d with Pd(OAc)2 in a 1:2 ratio, in the absence of NaBr, gave complexes trans-[PdBr2(NHC)2] (7). All compounds were fully characterized by NMR spectroscopy, mass spectrometry (MALDI), and elemental analysis. In addition, the molecular structures of 2c, 3c, 3d, and 5b were determined by X-ray diffraction. The catalytic activities of 2–7 in Mizoroki–Heck C–C coupling reactions of aryl halides with n-butyl acrylate are described and compared. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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