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Green Synthesis of Palladium Nanoparticles: Applications in Aryl Halide Cyanation and Hiyama Cross-Coupling Reaction Under Ligand Free Conditions

Abstract

In the current work, palladium nanoparticles (Pd NPs) were prepared from palladium acetate biogenically using the aqueous-ethanolic extract of black pepper (Piper nigrum) and characterized by various analytical techniques like XRD, FE-SEM, EDS, TEM, ATR-IR, UV–Vis spectroscopy, BET, TGA and ICP-OES analysis. The reduction of Pd(II) to Pd(0) is achieved by the action of various phytochemicals present in the black pepper extract like phenols, acids, pellitorine, ethyl piperonyl cyanoacetate, piperine and N-isobutyl-tetradeca-2,4-dienamide. The biosynthesized Pd NPs shown excellent catalytic activity in aryl halide cyanation and Hiyama cross-coupling reactions. Also, less toxic potassium hexacyanoferrate(II) trihydrate was used as cyanide source in aryl halide cyanation and Hiyama cross-coupling was performed under fluoride free condition. Both reactions proceeded well with Pd NPs under ligand free circumstances to give good to excellent yields. The Pd NPs were recovered after each reaction and recycled up to five times in aryl halide cyanation and ten times in Hiyama cross-coupling without considerable loss in the activity.

Graphical Abstract

Green synthesis of palladium nanoparticles: applications in aryl halide cyanation and Hiyama cross-coupling reaction under ligand free conditions.

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Acknowledgements

The authors thank Nano Mission, Ministry of Science & Technology, Department of Science & Technology, Government of India, for financial support through the Grant SR/NM/NS-20/2014. Authors also thank SAIF, CUSAT and SAIF, IITM for the analytical support.

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Correspondence to Siddappa A. Patil.

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Kandathil, V., Dateer, R.B., Sasidhar, B.S. et al. Green Synthesis of Palladium Nanoparticles: Applications in Aryl Halide Cyanation and Hiyama Cross-Coupling Reaction Under Ligand Free Conditions. Catal Lett 148, 1562–1578 (2018). https://doi.org/10.1007/s10562-018-2369-5

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  • DOI: https://doi.org/10.1007/s10562-018-2369-5

Keywords

  • Biogenic synthesis
  • Piper nigrum
  • Palladium nanoparticles
  • Cyanation reaction
  • Hiyama cross-coupling
  • Recycle