Synthetic studies for the 1,3-iterative organoiron approach to the synthesis of siculinine: efficient arylation using a diarylcuprate reagent

George Stephenson, Ian M. Palotai, Sarah Thomas, Michael Tinkl

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Abstract

Disubstituted (cyclohexadienyl)iron(1+) complex 2b is prepared by an improved route that starts from 1,2-dimethoxycyclohexa-1,4-diene 3. In five steps, the synthesis of 2b is achieved by complexation with Fe(CO)5, hydride abstraction,
hydrolysis, addition of EtO2CCH2ZrBr, and reaction with HBF4. In the presence of dimethyl sulfide, the reaction of 2b with 2-[CH2N(CH2CH=CH2)2]-functionalized diarylcuprate reagent 7 gave the 5α-arylcyclohexadiene complex 1b in 88% yield. A DFT study compared diarylzinc and diarylcuprate reagents containing chelating CH2NMe2 substituents.
Original languageEnglish
Pages (from-to)1895–1901
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2013
Issue number10
Early online date18 Feb 2013
DOIs
Publication statusPublished - Apr 2013

Keywords

  • Synthesis design
  • Arylation
  • C–C coupling
  • Alkaloids
  • Regioselectivity
  • Iron
  • Copper
  • Density functional calculations

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