Benzene → S-(trifluoromethyl)phenyl-2-trifluoromethylthiophenylsulfonium Triflate

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Reaction Steps

S-(trifluoromethyl)phenyl-2-trifluoromethylthiophenylsulfonium triflate (17) was synthesized as shown in FIG. 11. 1,2-Diiodobenzene was converted to phenyl 1,2-bis(trifluoromethyl sulfide) (14) in 84% yield. Compound 14 was oxidized to phenyl 1,2-bis(trifluoromethyl sulfoxide) (15) under reflux. No sulfone was isolated with the only by-product being phenyl 2-trifluoromethylthio trifluoromethyl sulfoxide (16). It is likely that a bulk steric effect hindered further oxidation and the reaction stopped at the sulfoxide stage. Compound 15 reacted with benzene and Tf2O to give the product S-(trifluoromethyl)phenyl-2-trifluoromethylthiophenylsulfonium triflate (17).

Provenance & Evidence