1,4-Butanediol as a reducing agent in transfer hydrogenation reactions

Chem Asian J. 2010 Mar 1;5(3):538-42. doi: 10.1002/asia.200900527.

Abstract

1,4-Butanediol is able to deliver two equivalents of H(2) in hydrogen-transfer reactions to ketones, imines, and alkenes. Unlike simple alcohols, which establish equilibrium in the reduction of ketones, 1,4-butanediol acts essentially irreversibly owing to the formation of butyrolactone, which acts as a thermodynamic sink. It is therefore not necessary to use 1,4-butanediol in great excess in order to achieve reduction reactions. In addition, allylic alcohols are reduced to saturated alcohols through an isomerization/reduction sequence using a ruthenium catalyst with 1,4-butanediol as the reducing agent. Imines and alkenes are also reduced under similar conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Butylene Glycols / chemistry*
  • Hydrogenation
  • Imines / chemistry
  • Isomerism
  • Lactones / chemistry
  • Propanols / chemistry
  • Reducing Agents / chemistry*
  • Ruthenium / chemistry

Substances

  • Alkenes
  • Butylene Glycols
  • Imines
  • Lactones
  • Propanols
  • Reducing Agents
  • allyl alcohol
  • Ruthenium
  • 1,4-butanediol