Ni(0)-Catalyzed Dimerization of o-Keto Carboxylic Acid Pseudochlorides
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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.
Keywordsacid pseudochlorides dimerization catalysis 3,3′-diphthalides diastereoisomers
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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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