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Water-soluble palladacycles containing hydroxymethyl groups: synthesis, crystal structures and use as catalysts for amination and Suzuki coupling of reactions

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Abstract

Two water-soluble monophosphine [PPh3 and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl(Sphos)]-palladacycles containing hydroxymethyl groups 2–3 were prepared by cyclopalladation and chloride bridge-splitting reactions. The complexes were characterized by elemental analysis, ESI–MS and NMR. In addition, single-crystal X-ray analysis reveals that they have one-dimensional lamellar structures involving intermolecular hydrogen bonds and π–π interactions. The use of these palladacycles as catalysts for amination and Suzuki coupling of aryl chlorides in water was investigated. Complex 3 was found to be very efficient for these coupling reactions. Additionally, it was also successfully used in Suzuki coupling of (hydroxymethyl)phenylboronic acid for the synthesis of substituted 2-N-heterocyclic biarylmethanols.

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Acknowledgments

We are grateful to the Innovation Scientists and Technicians Troop Construction Projects of Henan Province (154100510015), the tackle key problem of science and technology Project of Henan Province (162102210125) and the Science Foundation of Henan Education Department (14A150049 and 15B150008).

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Authors and Affiliations

  1. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, 450052, Henan, China

    Xin Han, Zhi-Qiang Xiao, Xin-Qi Hao & Mao-Ping Song

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

    Hong-Mei Li, Chen Xu, Zhi-Qiang Wang & Wei-Jun Fu

  3. College of Food and Pharmacy, Luoyang Normal University, Luoyang, 471022, Henan, China

    Chen Xu

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  1. Xin Han
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Correspondence to Chen Xu or Xin-Qi Hao.

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Han, X., Li, HM., Xu, C. et al. Water-soluble palladacycles containing hydroxymethyl groups: synthesis, crystal structures and use as catalysts for amination and Suzuki coupling of reactions. Transition Met Chem 41, 403–411 (2016). https://doi.org/10.1007/s11243-016-0036-5

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