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NNN pincer palladium(II) complexes with N-(2-(1H-pyrazol-1-yl)phenyl)-picolinamide ligands: synthesis, characterization, and application to heck coupling reaction

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Abstract

N-(2-(1H-pyrazol-1-yl)phenyl)-picolinamide ligands 3a–c and 5a–f have been easily prepared from commercially available 2-pyridinecarboxylic acid. Reaction of 3a–c and 5a–f with PdCl2 in toluene in the presence of triethylamine gave the nine NNN pincer Pd(II) complexes 6a–i in 15–91% yields. All the new compounds were characterized by 1H, 13C NMR spectra and HRMS. In addition, the molecular structures of complexes 6a and 6i have also been determined by single-crystal X-ray diffraction. The obtained palladium(II) catalysts showed efficient catalytic activity toward the Heck coupling of aryl bromides with styrenes. Under the condition of 5% catalyst loading, the expected various styrenes were obtained in moderate to high yields (up to 99% yield).

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Acknowledgements

We are grateful to the Key Science Research of Education Committee in Henan Province (19A150035), the Key Scientific and Technological Project of Henan Province (192102110222), the Foundation for University Young Key Teacher of Henan Province (2021GGJS136), the Program for Science & Technology Innovation Talents in Universities of Henan Province (14HASTIT016) and the Program of Science and Technology Innovation Talents of Henan Province (No. 2018JQ0011).

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T.W., F.L., and H.J. wrote the main manuscript text. Y.L., S.L., Y.Z., and J. W. prepared experimental part. All authors reviewed the manuscript.

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Correspondence to Tao Wang or Heng Jiang.

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Xu, Y., Wang, T., Li, Y. et al. NNN pincer palladium(II) complexes with N-(2-(1H-pyrazol-1-yl)phenyl)-picolinamide ligands: synthesis, characterization, and application to heck coupling reaction. Transit Met Chem 49, 149–159 (2024). https://doi.org/10.1007/s11243-023-00570-7

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