Iminoiodane- and Brønsted 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 Leung, Edmond Dik Lung MA, Philip Wai Hong Chan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 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 - 1 Jul 2015

Scopus Subject Areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

User-Defined Keywords

  • 1,3-dicarbonyl compounds
  • C-C bond formation
  • Cross dehydrogenation coupling
  • Iminoiodanes
  • Metal-free catalysis

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