Catalytic C-H α-trifluoromethylation of α,β-unsaturated carbonyl compounds

Org Lett. 2014 Mar 7;16(5):1522-5. doi: 10.1021/ol5004498. Epub 2014 Feb 20.

Abstract

A copper(I)-catalyzed, regioselective C-H α-trifluoromethylation of α,β-unsaturated carbonyl compounds using Togni's reagent was developed. Diverse substrates, including enones as well as α,β-unsaturated esters, thioesters, and amides, stereospecifically afforded the corresponding (E)-α-trifluoromethylated products in moderate to high yields. Further, this method was applied to the C-H trifluoromethylation of drugs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Catalysis
  • Copper / chemistry*
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Indicators and Reagents
  • Iodides / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Amides
  • Hydrocarbons, Fluorinated
  • Indicators and Reagents
  • Iodides
  • Ketones
  • Copper
  • cuprous iodide