Reactivity of a hypervalent iodine trifluoromethylating reagent toward THF: ring opening and formation of trifluoromethyl ethers.
1-Trifluoromethyl-1,2-benziodoxol-3-(1H)-one (1) is able to transfer the electrophilic CF(3) group to the oxygen atom of THF in the presence of a Lewis or Bronsted 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.
Fantasia
Serena
S
Department of Chemistry and Applied Bioscience, Swiss Federal Institute of Technology, ETH Zurich, 8093 Zurich, Switzerland.
Welch
Jan M
JM
Togni
Antonio
A
D002384:Catalysis; D003500:Cyclization; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis / Q000737:chemistry*; D007202:Indicators and Reagents; D007455:Iodine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D015394:Molecular Structure; D013329:Structure-Activity Relationship
C546303:1-trifluoromethyl-1,2-benziodoxol-3(1H)-one; D004987:Ethers; D006845:Hydrocarbons, Fluorinated; D006846:Hydrocarbons, Halogenated; D007202:Indicators and Reagents; D007455:Iodine