Iron/tetramethylethylenediamine-catalyzed ambient-temperature coupling of alkyl Grignard reagents and aryl chlorides

J Org Chem. 2013 Sep 20;78(18):9517-21. doi: 10.1021/jo4016612. Epub 2013 Sep 12.

Abstract

Tetramethylethylenediamine (TMEDA) acts as cheap and readily removed ligand in the iron-catalyzed coupling of alkyl Grignard reagents and activated aryl chlorides. The use of TMEDA allows for low ligand and iron catalyst loading as well as an increased reaction concentration and an ambient reaction temperature on a mole scale.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry
  • Catalysis
  • Esters / chemical synthesis
  • Esters / chemistry
  • Ethylenediamines / chemistry*
  • Hydrocarbons, Chlorinated / chemistry*
  • Iron / chemistry*
  • Ligands
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Temperature*

Substances

  • Amides
  • Esters
  • Ethylenediamines
  • Hydrocarbons, Chlorinated
  • Ligands
  • Organometallic Compounds
  • N,N,N',N'-tetramethylethylenediamine
  • Iron