Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions

Molecules. 2019 Jan 28;24(3):459. doi: 10.3390/molecules24030459.

Abstract

Functionalization of amide bond via the cleavage of a non-carbonyl, C-N σ bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N σ bond cleavage of N-acylazetidines using the electride derived from sodium dispersions and 15-crown-5. Of note, less strained cyclic amides and acyclic amides are stable under the reaction conditions, which features the excellent chemoselectivity of the reaction. This method is amenable to a range of unhindered and sterically encumbered azetidinyl amides.

Keywords: C-N σ bond cleavage; amides; crown ether; sodium.

MeSH terms

  • Amides / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nitrogen / chemistry*
  • Sodium / chemistry

Substances

  • Amides
  • Carbon
  • Sodium
  • Nitrogen