Acid-mediated formation of trifluoromethyl sulfonates from sulfonic acids and a hypervalent iodine trifluoromethylating agent.
A variety of sulfonic acids have been trifluoromethylated using 1-trifluoromethyl-1,2-benziodoxol-3(1H)-one under mild conditions in good to excellent yields. Initial mechanistic investigations of this reaction show a clean second-order kinetics and only very weak substrate electronic effects.
Koller
Raffael
R
Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zurich, 8093 Zurich, Switzerland.
Huchet
Quentin
Q
Battaglia
Philip
P
Welch
Jan M
JM
Togni
Antonio
A
D000476:Alkanesulfonates / Q000737:chemistry*; D000498:Allyl Compounds; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007455:Iodine; D008745:Methylation; D015394:Molecular Structure; D013451:Sulfonic Acids / Q000737:chemistry*
C546303:1-trifluoromethyl-1,2-benziodoxol-3(1H)-one; D000476:Alkanesulfonates; D000498:Allyl Compounds; D006846:Hydrocarbons, Halogenated; D013451:Sulfonic Acids; D007455:Iodine