N-heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates

Org Lett. 2014 Nov 7;16(21):5678-81. doi: 10.1021/ol5027415. Epub 2014 Oct 24.

Abstract

An unprecedented N-heterocyclic carbene catalytic reductive β,β-carbon coupling of α,β-nitroalkenes, by using an organic substrate to mimic the one-electron oxidation role of the pyruvate ferredoxin oxidoreductase (PFOR) in living systems, has been developed. The reaction goes through a radical anion intermediate generated under a catalytic redox process. For the first time, the presence of radical anion intermediate in NHC organocatalysis is observed and clearly verified.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Anions / chemistry*
  • Electrons
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Nitro Compounds / chemistry*
  • Pyruvate Synthase / chemistry*

Substances

  • Alkenes
  • Anions
  • Nitro Compounds
  • carbene
  • Pyruvate Synthase
  • Methane