Catalyzing the Hydrodefluorination of CF3-Substituted Alkenes by PhSiH3. H• Transfer from a Nickel Hydride

J Am Chem Soc. 2020 Mar 11;142(10):4793-4799. doi: 10.1021/jacs.9b13757. Epub 2020 Jan 24.

Abstract

The hydrodefluorination of CF3-substituted alkenes can be catalyzed by a nickel(II) hydride bearing a pincer ligand. The catalyst loading can be as low as 1 mol%. gem-Difluoroalkenes containing a number of functional groups can be formed in good to excellent yields by a radical mechanism initiated by H• transfer from the nickel hydride. The relative reactivity of various substrates supports the proposed mechanism, as does a TEMPO trapping experiment.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkenes / chemical synthesis*
  • Catalysis
  • Coordination Complexes / chemistry*
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Models, Chemical
  • Molecular Structure
  • Nickel / chemistry*
  • Silanes / chemistry*

Substances

  • Alkenes
  • Coordination Complexes
  • Hydrocarbons, Fluorinated
  • Silanes
  • Nickel