Controlled trifluoromethylation reactions of alkynes through visible-light photoredox catalysis

Angew Chem Int Ed Engl. 2014 Jan 7;53(2):539-42. doi: 10.1002/anie.201308735. Epub 2013 Nov 20.

Abstract

The control of a reaction that can form multiple products is a highly attractive and challenging concept in synthetic chemistry. A set of valuable CF3 -containing molecules, namely trifluoromethylated alkenyl iodides, alkenes, and alkynes, were selectively generated from alkynes and CF3 I by environmentally benign and efficient visible-light photoredox catalysis. Subtle differences in the combination of catalyst, base, and solvent enabled the control of reactivity and selectivity for the reaction between an alkyne and CF3 I.

Keywords: iridium; radical reactions; ruthenium; trifluoromethylation; visible light.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry
  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Catalysis
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Hydrocarbons, Iodinated / chemical synthesis
  • Hydrocarbons, Iodinated / chemistry
  • Light*
  • Methylation
  • Molecular Structure
  • Oxidation-Reduction
  • Photochemistry

Substances

  • Alkenes
  • Alkynes
  • Hydrocarbons, Fluorinated
  • Hydrocarbons, Iodinated