Indium-copper and indium-silver mediated barbier-grignard-type alkylation reaction of aldehydes using unactivated alkyl halides in water

J Org Chem. 2008 May 16;73(10):3922-4. doi: 10.1021/jo8000589. Epub 2008 Apr 9.

Abstract

An efficient method has been developed for the Barbier-Grignard-type alkylation reaction of aldehydes (including aliphatic version) using unactivated alkyl halides in water in the presence of an In/CuI/I(2) or In/AgI/I(2) system. The reactions proceeded more efficiently in water than in organic solvent. In, CuI or AgI, and I(2) were all essential for the efficient progress of the reactions. A radical-type reaction mechanism was studied and proposed by using 4-pentenal as substrate.

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Aldehydes / chemistry*
  • Alkylation
  • Copper / chemistry*
  • Hydrocarbons, Halogenated / chemistry*
  • Indium / chemistry*
  • Molecular Structure
  • Silver / chemistry*
  • Stereoisomerism
  • Water / chemistry

Substances

  • Alcohols
  • Aldehydes
  • Hydrocarbons, Halogenated
  • Indium
  • Water
  • Silver
  • Copper