Fe(III)-catalyzed bicyclization of yne-allenones with indoles for the atom-economic synthesis of 3-indolyl cyclobutarenes

Heng Li, Wen Juan Hao, Guigen Li, Shu Jiang Tu, Bo Jiang

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3 Scopus citations

Abstract

A new Fe(III)-catalyzed bicyclization reaction of yne-allenones with indoles has been established, enabling the direct construction of cyclobuta[a]naphthalen-4-ols with an all-carbon quaternary center in good to excellent yields. This reaction was performed by using low-cost FeCl3 as the catalyst and EtOH as the environmentally benign solvent, providing a green protocol for constructing the cyclobutarene framework with a high degree of atom economy and functional group compatibility. The reaction mechanism was proposed to proceed through a [2 + 2] cycloaddition/1,6-conjugate addition cascade.

Original languageEnglish
Article number599
JournalFrontiers in Chemistry
Volume6
Issue numberDEC
DOIs
StatePublished - 2018

Keywords

  • 1,6-addition
  • Bicyclization
  • Cyclobutarenes
  • Fe(III)-catalysis
  • Yne-allenones

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