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Electrochemical properties of diphosphonate-bridged palladacycles and their reactivity in arene phosphonation

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Abstract

A series of diphosphonate-bridged dipalladacycles [(phpy)Pd(EtO)2P(O)]2, [(bhq)Pd(EtO)2P(O)]2, [(phpz)Pd(EtO)2P(O)]2 (phpy=2-phenylpyridine, bhq=benzo[h]quinoline, phpz=1-phenylpyrazole), which are known to be involved in catalytic C–H phosphonation reactions, was prepared and characterized by NMR spectroscopy and cyclic voltammetry in acetonitrile solutions and in carbon paste electrode. Diphosphonate dipalladacycles are oxidized irreversibly at more positive potentials as distinguished from related acetate palladacycles. Electrochemical preparative oxidations carried out under mild conditions without any specially added oxidants quantitatively afforded corresponding arylphosphonates. For complete conversion of dipalladacycles into arylphosphonates, four electrons per each palladium atom are required, that probably indicates a mechanism involving Pd(IV)/Pd(II) redox couple.

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Acknowledgments

The work is supported by the Russian Science Foundation (grant no. 14-23-00016).

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Authors and Affiliations

  1. A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of Russian Academy of Sciences, 8, Arbuzov str., 420088, Kazan, Russian Federation

    Tatyana Gryaznova, Yulia Dudkina, Mikhail Khrizanforov, Oleg Sinyashin, Olga Kataeva & Yulia Budnikova

Authors
  1. Tatyana Gryaznova
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  2. Yulia Dudkina
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  3. Mikhail Khrizanforov
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  4. Oleg Sinyashin
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  5. Olga Kataeva
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  6. Yulia Budnikova
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Corresponding author

Correspondence to Yulia Budnikova.

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Gryaznova, T., Dudkina, Y., Khrizanforov, M. et al. Electrochemical properties of diphosphonate-bridged palladacycles and their reactivity in arene phosphonation. J Solid State Electrochem 19, 2665–2672 (2015). https://doi.org/10.1007/s10008-015-2875-y

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  • DOI: https://doi.org/10.1007/s10008-015-2875-y

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