Selective reduction of ketones using water as a hydrogen source under high hydrostatic pressure

Org Biomol Chem. 2012 Sep 28;10(36):7321-6. doi: 10.1039/c2ob25941a.

Abstract

A selective reduction of a broad variety of ketones is described. The method is based on the combination of a Ni-Al alloy and high hydrostatic pressure (HHP, 2.8 kbar) in an aqueous medium. The reaction of the Ni-Al alloy with water provides in situ hydrogen generation and the high pressure ensures that the H(2) formed remains in the solution, thus the C=O reduction readily occurs. The application of the HHP resulted in selective formation of the desired products and the common problem of non-selective overhydrogenation could be avoided. In most cases the reductions resulted in high yields and excellent selectivities without the use of any base.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis
  • Alcohols / chemistry
  • Aluminum / chemistry
  • Benzene Derivatives / chemical synthesis
  • Benzene Derivatives / chemistry
  • Hydrogen / chemistry*
  • Hydrostatic Pressure
  • Ketones / chemistry*
  • Molecular Structure
  • Nickel / chemistry
  • Oxidation-Reduction
  • Water / chemistry*

Substances

  • Alcohols
  • Benzene Derivatives
  • Ketones
  • Water
  • Nickel
  • Hydrogen
  • Aluminum