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Russian Journal of Organic Chemistry

, Volume 55, Issue 5, pp 670–677 | Cite as

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

  • T. A. Yangirov
  • A. A. Fatykhov
  • E. A. Sedova
  • N. G. Gileva
  • R. R. Khafizova
  • E. S. Meshcheryakova
  • L. M. Khalilov
  • V. A. KraikinEmail author
Article
  • 14 Downloads

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.

Keywords

acid pseudochlorides dimerization catalysis 3,3′-diphthalides diastereoisomers 

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Notes

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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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • T. A. Yangirov
    • 1
  • A. A. Fatykhov
    • 1
  • E. A. Sedova
    • 1
  • N. G. Gileva
    • 1
  • R. R. Khafizova
    • 1
  • E. S. Meshcheryakova
    • 2
  • L. M. Khalilov
    • 2
  • V. A. Kraikin
    • 1
    Email author
  1. 1.Ufa Institute of Chemistry, Ufa Federal Research CenterRussian Academy of Sciences (UIC UFRC RAS)Ufa, Republic of BashkortostanRussia
  2. 2.Institute of Petrochemistry and Catalysis UFRC RASUfa, Republic of BashkortostanRussia

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