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N-heterocyclic carbene adducts of cyclopalladated ferrocenylchloropyrimidine: synthesis, structural characterization and application in the Sonogashira reaction

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Abstract

Three N-heterocyclic carbene (NHC) adducts of cyclopalladated ferrocenylchloropyrimidine, 2–4 [PdCl{[(η5-C5H5)]Fe[(η5-C5H3)-N2C4H2-Cl]}(NHCs)] have been prepared by reaction of the chloride-bridged palladacyclic dimer 1 [PdCl{[(η5-C5H5)]Fe[(η5-C5H3)-N2C4H2-Cl]}]2 with the corresponding imidazolium salts. These complexes were characterized by elemental analysis, IR, ESI–MS and NMR. The use of these complexes as catalysts for the Sonogashira reaction was examined. Complex 4 proved to be an efficient catalyst for the Sonogashira reaction of aryl bromides and some activated aryl chlorides under copper- and amine-free conditions. Typically, using 0.1–2 mol % of catalyst in the presence of 1.5 equivalents of CsOAc as base in dimethylacetamide at 120 °C provided coupling products in good yields.

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Acknowledgments

We are grateful to the National Natural Science Foundation of China (No. 20902043) and the Natural Science Foundation of Henan Province and Henan Education Department, China (No. 102300410220 and 2009B150019) for financial support of this work.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, 471022, Henan, China

    Chen Xu, Xin-Hua Lou, Zhi-Qiang Wang & Wei-Jun Fu

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  1. Chen Xu
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  2. Xin-Hua Lou
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  3. Zhi-Qiang Wang
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  4. Wei-Jun Fu
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Correspondence to Chen Xu.

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Xu, C., Lou, XH., Wang, ZQ. et al. N-heterocyclic carbene adducts of cyclopalladated ferrocenylchloropyrimidine: synthesis, structural characterization and application in the Sonogashira reaction. Transition Met Chem 37, 519–523 (2012). https://doi.org/10.1007/s11243-012-9617-0

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