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Ni(0)-Catalyzed Dimerization of o-Keto Carboxylic Acid Pseudochlorides

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Abstract

A new protocol of the synthesis of 3,3′-diaryl-3,3′-diphthalides by dehalogenation of o-keto carboxylic acid pseudochlorides is implemented. The feature of the new protocol is that the reaction is carried out in the presence of a zero-valent nickel complex catalyst generated in situ by mixing zinc powder, nickel(II) chloride, triphenylphosphine, and 2,2′-bipyridine. Along with the target dimerization products of pseudochlorides, minor products were isolated, whose structure allowed to propose possible schemes of side reactions.

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Acknowledgments

The elemental analyses, IR and NMR spectra were obtained and semipreparative HPLC separation was performed at the “Khimiya Center for Collective Use”, Ufa Institute of Chemistry UFRC RAS. X-ray diffraction analysis was performed at the Agidel Center for Collective Use, Institute of Petrochemistry and Catalysis UFRC RAS.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences (UIC UFRC RAS), pr. Oktyabrya 69, Ufa, Republic of Bashkortostan, 450054, Russia

    T. A. Yangirov, A. A. Fatykhov, E. A. Sedova, N. G. Gileva, R. R. Khafizova & V. A. Kraikin

  2. Institute of Petrochemistry and Catalysis UFRC RAS, pr. Oktyabrya 141, Ufa, Republic of Bashkortostan, 450075, Russia

    E. S. Meshcheryakova & L. M. Khalilov

Authors
  1. T. A. Yangirov
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  2. A. A. Fatykhov
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  3. E. A. Sedova
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  4. N. G. Gileva
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  5. R. R. Khafizova
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  6. E. S. Meshcheryakova
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  7. L. M. Khalilov
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  8. V. A. Kraikin
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Corresponding author

Correspondence to V. A. Kraikin.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 5, pp. 773–781.

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Yangirov, T.A., Fatykhov, A.A., Sedova, E.A. et al. Ni(0)-Catalyzed Dimerization of o-Keto Carboxylic Acid Pseudochlorides. Russ J Org Chem 55, 670–677 (2019). https://doi.org/10.1134/S1070428019050142

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  • DOI: https://doi.org/10.1134/S1070428019050142

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