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Binaphthyl-bridged bis-imidazolinium salts as N-heterocyclic carbene ligand precursors in the palladium-catalyzed Heck reaction

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Abstract

Two new bis-imidazolinium salts (4a, 4b) have been synthesized as precursors of N-heterocyclic carbenes (NHCs) from the commercially available (R)-2,2′-dihydroxy-1,1′-binaphthalene. The two bis-imidazolinium salts were used as efficient precursor of NHC ancillary ligands in the palladium-catalyzed Heck reaction. Good to excellent yields and high stereoselectivities were obtained with ethyl acrylate, acrylonitrile, and acrylamide as starting materials. The structure of bis-imidazolinium salt 4b was further characterized by single crystal X-ray diffraction analysis.

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Authors and Affiliations

  1. Key Laboratory of Mesoscopic Chemistry of Ministry of Education; School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China

    Hui Wu, Can Jin, GuoLi Huang, LianJun Wang, JuLi Jiang & LeYong Wang

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  1. Hui Wu
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  2. Can Jin
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  3. GuoLi Huang
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  4. LianJun Wang
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  6. LeYong Wang
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Correspondence to JuLi Jiang or LeYong Wang.

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Wu, H., Jin, C., Huang, G. et al. Binaphthyl-bridged bis-imidazolinium salts as N-heterocyclic carbene ligand precursors in the palladium-catalyzed Heck reaction. Sci. China Chem. 54, 951–956 (2011). https://doi.org/10.1007/s11426-011-4272-4

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