Minimizing the amount of nitromethane in palladium-catalyzed cross-coupling with aryl halides

J Org Chem. 2013 Sep 6;78(17):8859-64. doi: 10.1021/jo401249y. Epub 2013 Aug 13.

Abstract

A method for the formation of arylnitromethanes is described that employs readily available aryl halides or triflates and small amounts of nitromethane in a dioxane solvent, thereby reducing the hazards associated with this reagent. Specifically, 2-10 equiv (1-5% v/v) of nitromethane can be employed in comparison to prior work that used nitromethane as solvent (185 equiv). The present transformation provides high yields at relatively low temperatures and tolerates an array of functionality, including heterocycles and substantial steric encumbrance.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Hydrocarbons, Halogenated / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemical synthesis
  • Methane / chemistry
  • Molecular Structure
  • Nitroparaffins / chemical synthesis*
  • Nitroparaffins / chemistry
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • Hydrocarbons, Halogenated
  • Nitroparaffins
  • Palladium
  • Methane
  • nitromethane