One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using aldehydes

J Org Chem. 2007 Dec 7;72(25):9815-7. doi: 10.1021/jo701503q. Epub 2007 Nov 13.

Abstract

One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using various aldehydes by Pd/C catalyst in aqueous 2-propanol solvent with ammonium formate as in situ hydrogen donor is illustrated. The reaction proceeded smoothly and selectively with excellent yield at room temperature. Our protocol presents a facile, economical, and environmentally benign alternative for reductive amination.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Alkylation
  • Amines / chemical synthesis*
  • Aniline Compounds / chemical synthesis*
  • Aniline Compounds / chemistry*
  • Carbon / chemistry
  • Catalysis
  • Molecular Structure
  • Nitrobenzenes / chemistry*
  • Oxidation-Reduction
  • Palladium / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Amines
  • Aniline Compounds
  • Nitrobenzenes
  • Palladium
  • Carbon