Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate

The Uses of Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate

Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate

Synthesis

Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate is synthesised using phenyl trifluoromethyl sulfoxide as a raw material by chemical reaction. The specific synthesis steps are as follows:
Trifluoromethyl sulfoxide (0.4 g, 2.1 mmol) and then benzene (4.9 g, 64 mmol) are introduced, under an inert atmosphere and at approximately 0° C. (lower limit below which benzene crystallizes), into a Schlenck tube purged beforehand with argon. Five equivalents of triflic anhydride (2.82 g, 10 mmol) are gradually added. The mixture is stirred for 1 h at 0° C. and then for 24 h at ambient temperature. The medium is evaporated and the residue is purified by chromatography with the CH3CN/CH2Cl2 (1/4) mixture as eluent. White crystals (Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate), having a melting point of 69-70° C., are obtained with a yield of 40%.

References

[1] J. MATSUO. A Convenient Method for the Synthesis of 2-Arylaziridines from Styrene Derivatives via 2-Arylethenyl(diphenyl)sulfonium Salts[J]. Chemistry Letters, 2003. DOI:10.1246/CL.2003.392.