Direct amide synthesis from either alcohols or aldehydes with amines: activity of Ru(II) hydride and Ru(0) complexes

J Org Chem. 2010 May 7;75(9):3002-6. doi: 10.1021/jo100254g.

Abstract

An in situ generated catalyst from readily available RuH(2)(PPh(3))(4), an N-heterocyclic carbene (NHC) precursor, NaH, and acetonitrile was developed. The catalyst showed high activity for the amide synthesis directly from either alcohols or aldehydes with amines. When a mixture of an alcohol and an aldehyde was reacted with an amine, both of the corresponding amides were obtained with good yields. Homogeneous Ru(0) complexes such as (eta(4)-1,5-cyclooctadiene)(eta(6)-1,3,5-cyclooctatriene)ruthenium [Ru(cod)(cot)] and Ru(3)(CO)(12) were also active in the amidation of an alcohol or an aldehyde with the help of an in situ generated NHC ligand.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Aldehydes / chemistry*
  • Amides / chemical synthesis*
  • Amines / chemistry*
  • Catalysis
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Ruthenium / chemistry*

Substances

  • Alcohols
  • Aldehydes
  • Amides
  • Amines
  • Organometallic Compounds
  • Ruthenium