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Electrochemical C-H phosphorylation of 2-phenylpyridine in the presence of palladium salts

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Abstract

A new approach was developed to the introduction of the phosphonate group into arylpyridines using 2-phenylpyridine as an example. The approach is the electrochemical oxidation of a mixture of 2-phenylpyridine, diethyl phosphite, and palladium acetate at room temperature. An intermediate dipalladium cyclic complex was isolated that is formed by the ortho-palladation of 2-phenylpyridine and substitution of acetate ions by phosphonate ions. The preparative oxidation of this complex selectively results in the product of the phosphorylation of the C-H bond in 2-phenylpyridine.

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Authors and Affiliations

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

    Yu. B. Dudkina, T. V. Gryaznova, O. N. Kataeva, Yu. H. Budnikova & O. G. Sinyashin

Authors
  1. Yu. B. Dudkina
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  2. T. V. Gryaznova
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  3. O. N. Kataeva
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  4. Yu. H. Budnikova
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  5. O. G. Sinyashin
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Corresponding author

Correspondence to T. V. Gryaznova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2641—2646, December, 2014.

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Dudkina, Y.B., Gryaznova, T.V., Kataeva, O.N. et al. Electrochemical C-H phosphorylation of 2-phenylpyridine in the presence of palladium salts. Russ Chem Bull 63, 2641–2646 (2014). https://doi.org/10.1007/s11172-014-0792-3

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  • DOI: https://doi.org/10.1007/s11172-014-0792-3

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