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Ligand-directed electrochemical functionalization of C(sp2)—H bonds in the presence of the palladium and nickel compounds

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Abstract

The recent achievements of electrochemical functionalization of C—H bonds in aromatic substrates containing the pyridine moiety and acting as a ligand directing substitution to the ortho-position in the presence of the palladium and nickel compounds are analyzed and generalized in the review. Acetoxylation, perfluoroacetoxylation, perfluoroalkylation, and phosphorylation are considered for 2-phenylpyridine (PhPy) as an example. The PdII metallocycles with the Pd-bound acetate, perfluoroacetate, and perfluoroheptanoate substituents were isolated and characterized as possible intermediates: binuclear [(PhPy)Pd(µ-OAc)]2 and [(PhPy)Pd(µ-TFA)]2 and mononuclear [(PhPy)Pd(TFA)](MeCN), [(PhPy)Pd(TFA)](PhPy), [(PhPy)Pd(PFH)](PhPy), and [(PhPy)Pd(EtO)2P(O)]2. Their electrochemical properties were studied. The fluorinated derivatives are in solvent-dependent equilibrium between the mononuclear and binuclear forms. Cyclic voltammetry was used to establish the redox properties of the palladium cycles and routes of their oxidation to the final products. A new approach to CH-substitution products based on the electrochemical generation of Pd or Ni in high oxidation states in the presence of substrate-ligand was proposed.

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Authors and Affiliations

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

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

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  1. Yu. B. Dudkina
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  2. T. V. Gryaznova
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  3. O. G. Sinyashin
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  4. Yu. H. Budnikova
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Correspondence to Yu. H. Budnikova.

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Based on the materials of the XXVI International Chugaev Conference on Coordination Chemistry (October 6—10, 2014, Kazan).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1713—1725, August, 2015.

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Dudkina, Y.B., Gryaznova, T.V., Sinyashin, O.G. et al. Ligand-directed electrochemical functionalization of C(sp2)—H bonds in the presence of the palladium and nickel compounds. Russ Chem Bull 64, 1713–1725 (2015). https://doi.org/10.1007/s11172-015-1067-3

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  • DOI: https://doi.org/10.1007/s11172-015-1067-3

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