Catalytic MBH reaction of β-substituted nitroalkenes with azodicarboxylates

Org Biomol Chem. 2013 Sep 14;11(34):5722-6. doi: 10.1039/c3ob40804c.

Abstract

An unprecedented N-heterocyclic carbene (NHC) catalyzed Morita-Baylis-Hillman (MBH) reaction of β-substituted nitroalkenes and azodicarboxylates has been developed. Both β-aryl and β-alkyl nitroalkenes worked well for the reaction using 5 mol% of NHC catalyst, giving the desired α-hydrazino-α,β-unsaturated nitroalkenes in good to excellent yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Azo Compounds / chemistry*
  • Catalysis
  • Dicarboxylic Acids / chemistry*
  • Heterocyclic Compounds / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Nitro Compounds / chemistry*

Substances

  • Alkenes
  • Azo Compounds
  • Dicarboxylic Acids
  • Heterocyclic Compounds
  • Nitro Compounds
  • carbene
  • Methane