Copper- and iron-catalyzed decarboxylative tri- and difluoromethylation of α,β-unsaturated carboxylic acids with CF3SO2Na and (CF2HSO2)2Zn via a radical process

Org Lett. 2013 Jan 18;15(2):406-9. doi: 10.1021/ol3034059. Epub 2013 Jan 10.

Abstract

A copper-catalyzed decarboxylative trifluoromethylation of various α,β-unsaturated carboxylic acids by using a stable and inexpensive solid, sodium trifluoromethanesulfinate (CF(3)SO(2)Na, Langlois reagent), was developed. In addition, an iron-catalyzed difluoromethylation of aryl-substituted acrylic acids by using zinc difluoromethanesulfinate (DFMS, (CF(2)HSO(2))(2)Zn, Baran reagent) via a similar radical process was also achieved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Copper / chemistry*
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Indicators and Reagents
  • Iron / chemistry*
  • Molecular Structure
  • Stereoisomerism
  • Zinc / chemistry

Substances

  • Alkenes
  • Carboxylic Acids
  • Hydrocarbons, Fluorinated
  • Indicators and Reagents
  • Copper
  • Iron
  • Zinc