Direct trifluoromethylthiolation of unactivated C(sp(3))-H using silver(I) trifluoromethanethiolate and potassium persulfate

Angew Chem Int Ed Engl. 2015 Mar 23;54(13):4070-4. doi: 10.1002/anie.201411953. Epub 2015 Feb 23.

Abstract

A practical and efficient method for the direct trifluoromethylthiolation of unactivated C(sp(3) )H bonds by AgSCF3 /K2 S2 O8 under mild conditions is described. The reaction has a good functional-group tolerance and good selectivity. Initial mechanistic investigations indicate that the reaction may involve a radical process in which K2 S2 O8 plays key roles in both the activation of the C(sp(3) )H bond and the oxidation of AgSCF3 .

Keywords: CH activation; fluorine; radical reactions; synthetic methods; trifluoromethylthiolation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclooctanes / chemistry
  • Indicators and Reagents
  • Kinetics
  • Methylation
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction
  • Potassium Compounds / chemistry*
  • Sulfates / chemistry*
  • Sulfhydryl Compounds / chemical synthesis*

Substances

  • Cyclooctanes
  • Indicators and Reagents
  • Organometallic Compounds
  • Potassium Compounds
  • Sulfates
  • Sulfhydryl Compounds
  • potassium persulfate
  • cyclooctane