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Design, Synthesis and Characterization of Bimetallic Palladium Complexes for Terminal Olefin Epoxidation

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Abstract

A series of aromatic ring spaced binuclear Pd(II) complexes were synthesized from sterically tuned Schiff base ligands derived from 4,6-diacetylresorcinol and 2,6-dialkyl substituted anilines to provide a general and flexible set of complexes for terminal olefin epoxidation studies using “green” oxidant 30 % hydrogen peroxide as a terminal oxidant. All the compounds were fully characterized by analytical and spectrometric methods. Additionally, the ligands L1 and L2 were characterized by single crystal X-ray diffraction technique. The complexes C1 and C2 displayed high activity and substrate selectivity in the oxidation of 1-octene, whereas mixed products were observed in case of styrene with reasonable yields, arguably assignable to stringent steric and electronic factors of the complexes employed. Up to 98.5 % conversion is observed for epoxidation of 1-octene with high substrate selectivity, whereas up to 95 % conversion is observed for styrene with poor selectivity.

Graphical Abstract

A series of Pd(II) complexes were synthesized from sterically tuned Schiff base ligands derived from 4,6-diacetylresorcinol and 2,6-dialkyl substituted anilines to provide a flexible set of complexes for olefin epoxidation studies using hydrogen peroxide as a terminal oxidant. The complexes C1–C3 showed substrate selectivity in the oxidation of 1-octene, where as mixed products were observed in case of styrene with reasonable yields.

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Acknowledgments

The authors are thankful to USIC, Karnatak University, Dharwad, for providing spectral facilities. Recording of NMR and IR spectra from IISc-Bangalore and IIT-Bombay is gratefully acknowledged. One of the authors (Sandeep P. Netalkar) is thankful to Department of Science & Technology for providing financial assistance under INSPIRE fellowship program.

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Authors and Affiliations

  1. Department of Chemistry, Karnatak University, Pavate Nagar, Dharwad, 580 003, Karnataka, India

    Sandeep P. Netalkar & Vidyanand K. Revankar

  2. Department of Chemistry, Fergusson College, Pune, 411004, India

    Anupama A. Nevrekar

Authors
  1. Sandeep P. Netalkar
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  2. Anupama A. Nevrekar
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  3. Vidyanand K. Revankar
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Correspondence to Vidyanand K. Revankar.

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Netalkar, S.P., Nevrekar, A.A. & Revankar, V.K. Design, Synthesis and Characterization of Bimetallic Palladium Complexes for Terminal Olefin Epoxidation. Catal Lett 144, 1573–1583 (2014). https://doi.org/10.1007/s10562-014-1315-4

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  • DOI: https://doi.org/10.1007/s10562-014-1315-4

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