Reactivity of a Hypervalent Iodine Trifluoromethylating Reagent toward THF: Ring Opening and Formation of Trifluoromethyl Ethers
The Journal of Organic Chemistry2010Vol. 75(5), pp. 1779–1782
Citations Over TimeTop 10% of 2010 papers
Abstract
1-Trifluoromethyl-1,2-benziodoxol-3-(1H)-one (1) is able to transfer the electrophilic CF3 group to the oxygen atom of THF in the presence of a Lewis or Bro̷nsted acid. This results in a new ring-opening reaction of THF yielding trifluoromethyl ethers. Details of this reaction and the insight gained into the mechanism of action of reagent 1 are reported.
Related Papers
- → Mild electrophilic trifluoromethylation of secondary and primary aryl- and alkylphosphines using hypervalent iodine(iii)–CF3 reagents(2008)136 cited
- → Iodanes as Trifluoromethylation Reagents(2015)17 cited
- → ChemInform Abstract: Copper‐Catalyzed Trifluoromethylation of N,N‐Dialkylhydrazones.(2013)
- → ChemInform Abstract: Direct Synthesis of a Trifluoromethyl Copper Reagent from Trifluoromethyl Ketones: Application to Trifluoromethylation.(2014)
- → ChemInform Abstract: O‐Trifluoromethylation of N,N‐Disubstituted Hydroxylamines with Hypervalent Iodine Reagents.(2015)