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3,3'-((Arylmethylene)bis(4-methoxy-3,1-phenylene)) dipyridine derivatives as convenient ligands for Suzuki–Miyaura chemo- and homoselective cross-coupling reactions

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Abstract

Four novel N,N-bidentate triarylmethane-based ligands bearing β-pyridyl residues have been prepared and the catalytic activity of their in-situ generated palladium complexes were studied in the Suzuki–Miyaura cross-coupling reactions. Air and moisture stable 3,3'-((arylmethylene)bis(4-methoxy-3,1-phenylene))dipyridines L1-3 showed excellent activity in the Suzuki coupling reactions of aryl halides with aryl boronic acids under thermal and sonochemical reaction conditions. The described methodology provided good to high yields in short reaction times at ambient conditions. Moreover, it offered a straightforward way for Suzuki–Miyaura chemo- and homoselective cross-coupling of aryl halides with phenyl boronic acid. The structures of synthesized compounds were fully characterized by FT-IR, 1H-NMR, 13C-NMR, and elemental analyses. The coordination of palladium acetate to nitrogen sites of L1 was also studied using FTIR spectroscopy, EDX analysis and SEM observations.

Graphic abstract

The in-situ generated Pd-complexes of N,N-bidentate ligands L1-3 are described as robust and highly effective catalytic systems for the Suzuki cross-coupling of aryl halides with aryl boronic acids under thermal and sonochemical reaction conditions.

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Acknowledgements

We are grateful to the research council of the Vali-e-Asr University of Rafsanjan for financial support of this work.

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  1. Department of Chemistry, Vali-E-Asr University of Rafsanjan, Rafsanjan, 77176, Islamic Republic of Iran

    Raziyeh Hosseini & Reza Ranjbar-Karimi

  2. NMR Laboratory, Faculty of Science, Vali-E-Asr University of Rafsanjan, Rafsanjan, 77176, Islamic Republic of Iran

    Kazem Mohammadiannejad

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  1. Raziyeh Hosseini
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Correspondence to Reza Ranjbar-Karimi.

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Hosseini, R., Ranjbar-Karimi, R. & Mohammadiannejad, K. 3,3'-((Arylmethylene)bis(4-methoxy-3,1-phenylene)) dipyridine derivatives as convenient ligands for Suzuki–Miyaura chemo- and homoselective cross-coupling reactions. J IRAN CHEM SOC 19, 1143–1158 (2022). https://doi.org/10.1007/s13738-021-02373-y

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