One-pot synthesis of hypervalent iodine reagents for electrophilic trifluoromethylation

J Org Chem. 2013 Jul 5;78(13):6763-8. doi: 10.1021/jo400774u. Epub 2013 Jun 17.

Abstract

Simplified syntheses suited for large scale preparations of the two hypervalent iodine reagents 1 and 2 for electrophilic trifluoromethylation are reported. In both cases, the stoichiometric oxidants sodium metaperiodate and tert-butyl hypochlorite have been replaced by trichloroisocyanuric acid. Reagent 1 is accessible in a one-pot procedure from 2-iodobenzoic acid in 72% yield. Reagent 2 was prepared via fluoroiodane 11 in a considerably shorter reaction time and with no need of an accurate temperature control.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Hydrocarbons, Iodinated / chemical synthesis*
  • Hydrocarbons, Iodinated / chemistry
  • Indicators and Reagents / chemical synthesis*
  • Indicators and Reagents / chemistry
  • Methylation
  • Molecular Structure

Substances

  • Hydrocarbons, Fluorinated
  • Hydrocarbons, Iodinated
  • Indicators and Reagents