Metal-Free Formal Oxidative C-C Coupling by In Situ Generation of an Enolonium Species

Daniel Kaiser, Aurelien de la Torre, Saad Shaaban, Nuno Maulide (Corresponding author)

Publications: Contribution to journalArticlePeer Reviewed

Abstract

Much contemporary organic synthesis relies on transformations that are driven by the intrinsic, so-called “natural”, polarity of chemical bonds and reactive centers. The design of unconventionally polarized synthons is a highly desirable strategy, as it generally enables unprecedented retrosynthetic disconnections for the synthesis of complex substances. Whereas the umpolung of carbonyl centers is a well-known strategy, polarity reversal at the α-position of a carbonyl group is much rarer. Herein, we report the design of a novel electrophilic enolonium species and its application in efficient and chemoselective, metal-free oxidative C−C coupling.

Original languageEnglish
Pages (from-to)5921-5925
Number of pages5
JournalAngewandte Chemie (International Edition)
Volume56
Issue number21
DOIs
Publication statusPublished - 15 May 2017

Austrian Fields of Science 2012

  • 104015 Organic chemistry

Keywords

  • amide activation
  • chemoselectivity
  • keteniminium ions
  • oxidative C-C coupling
  • umpolung
  • ANION RELAY CHEMISTRY
  • ORGANOCATALYTIC SOMO REACTIONS
  • HYPERVALENT IODINE REAGENTS
  • SECONDARY AMIDES
  • ELECTROPHILIC ACTIVATION
  • CHEMOSELECTIVE SYNTHESIS
  • BOND FUNCTIONALIZATION
  • DIRECT TRANSFORMATION
  • PYRIDINE-DERIVATIVES
  • TRIFLIC ANHYDRIDE
  • oxidative C−C coupling

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