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Palladium(II) complexes of (t-butyl salicylidene) diphenyl disulfide diamine: synthesis, structure, spectral characterization and catalytic properties

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Abstract

The hexadentate N2S2O2 donor ligand N,N’-bis(3,5-tert-butylsalicylidene) diphenyl disulfide-2,2’-diamine was synthesised by the condensation of 2-aminophenyl disulfide and 3,5-di-tert-butyl-2-hydroxybenzaldehyde and its molecular structure was confirmed by X-ray studies. One of the tert-butyl groups in the Schiff base has rotational disorder around the C–C bond with ratio 0.56:0.44. The palladium complexes were prepared by the direct reaction of PdCl2(CH3CN)2 and Schiff base ligands N,N’-bis (5-tert-butylsalicylidene) diphenyl disulfide-2,2’-diamine and N,N’-bis(3,5-tert-butylsalicylidene) diphenyl disulfide-2,2’-diamine, respectively. The structure of the metal complexes was characterized by physico-chemical and spectroscopic methods. Palladium is in square-planar geometry bonded to imine nitrogen and phenolic O in both the complexes. The catalytic efficiency of the palladium complexes was evaluated in the cross-coupling reactions; Heck-Mizoroki reaction of iodobenzene and methyl acrylate and the Suzuki-Miyaura reaction of phenylboronic acid and iodobenzene, which gave low to moderate yields. Higher conversions were obtained for 2a as catalyst due to the increase in the number of bulky tertiary butyl groups in the structure.

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Funding

The authors receive support from University of Mauritius Grant for the submitted work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Mauritius, Reduit, Mauritius

    Minu G. Bhowon, Sabina Jhaumeer Laulloo, Sumayya Elaheebacus & Mounisha R. Dowlut

  2. Department of Chemistry, Nelson Mandela Metropolitan University, Summerstrand Campus South, Port Elizabeth, South Africa

    Eric C. Hosten

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  1. Minu G. Bhowon
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  2. Sabina Jhaumeer Laulloo
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  3. Eric C. Hosten
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  4. Sumayya Elaheebacus
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Correspondence to Minu G. Bhowon or Sabina Jhaumeer Laulloo.

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Bhowon, M.G., Jhaumeer Laulloo, S., Hosten, E.C. et al. Palladium(II) complexes of (t-butyl salicylidene) diphenyl disulfide diamine: synthesis, structure, spectral characterization and catalytic properties. Transit Met Chem 46, 537–545 (2021). https://doi.org/10.1007/s11243-021-00471-7

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  • DOI: https://doi.org/10.1007/s11243-021-00471-7

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