Silver-catalyzed oxidative activation of benzylic C-H bonds for the synthesis of difluoromethylated arenes

Angew Chem Int Ed Engl. 2014 Jun 2;53(23):5955-8. doi: 10.1002/anie.201400225. Epub 2014 Apr 23.

Abstract

A mild and catalytic method to form difluoromethylated arenes through the activation of benzylic C-H bonds has been developed. Utilizing AgNO3 as the catalyst, various arenes with diverse functional groups undergo activation/fluorination of benzylic C-H bonds with commercially available Selectfluor reagent as a source of fluorine in aqueous solution. The reaction is operationally simple and amenable to gram-scale synthesis.

Keywords: CH activation; arenes; fluorination; silver; synthetic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Fluorine / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Silver / chemistry*

Substances

  • Fluorine
  • Silver