Iminoiodane- and Bronsted base-mediated cross dehydrogenative coupling of cyclic ethers with 1,3-dicarbonyl compounds

Ciputra Tejo, Xiao Rong Sim, Bo Ra Lee, Benjamin James Ayers, Chung-Hang Duncan Leung, Dik-Lung Edmond Ma, Philip Wai Hong Chan

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5 Citations (Scopus)

Abstract

A one-pot, two-step approach to prepare 2-tetrahydrofuran and -pyran substituted 1,3-dicarbonyl compounds by PhI=NTs-mediated amination/Brønsted base-catalyzed cross dehydrogenative coupling (CDC) reaction of the cyclic ether and 1,3-dicarbonyl derivative under mild conditions is reported. The reaction is compatible with a variety of cyclic ethers and 1,3-dicarbonyl compounds, affording the corresponding coupled products in moderate to good yields of up to 80% over two steps
Original languageEnglish
Pages (from-to)13336-13353
Number of pages18
JournalMolecules
Volume20
Issue number7
DOIs
Publication statusPublished - 2015

Keywords

  • C–C bond formation
  • cross dehydrogenation coupling
  • 1,3-dicarbonyl compounds
  • iminoiodanes
  • metal-free catalysis

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