Cerium(IV) Trifluoromethanesulfonate


[107792-63-2]  · C4CeF12O12S4  · Cerium(IV) Trifluoromethanesulfonate  · (MW 736.34)

(oxidizing agent for benzyl alcohols and toluenes)

Alternate Name: ceric triflate.

Solubility: sol water, THF, DME, dioxane; insol dichloromethane, hexane, benzene.

Form Supplied in: yellow solid.

Preparative Methods: by the reaction of trifluoromethanesulfonic acid with freshly prepared cerium(IV) carbonate.1 The reagent can be prepared in situ by the electrochemical oxidation of Ce(OTf)3 in aqueous trifluoromethanesulfonic acid.2

Purification: thus far the reagent has only been used in crude form as prepared above.

Handling, Storage, and Precautions: the reagent is extremely hygroscopic and should be stored under strict absence of moisture. This reagent should be handled in a fume hood.

Oxidation of Benzyl Alcohols and Aryl Methyl Groups.

Benzyl alcohols are readily oxidized by Ce(OTf)4 in MeCN-H2O at room temperature to the corresponding benzaldehydes (eq 1).1 Under similar conditions, aryl methyl groups are converted to aldehydes in good yields (eq 2) (see also Cerium(IV) Ammonium Nitrate and Cerium(IV) Ammonium Sulfate).1 Ce(OTf)4 appears to be more reactive as an oxidizing agent than CAN or CAS.

1. Imamoto, T.; Koide, Y.; Hiyama, S. CL 1990, 1445.
2. Kreh, R. P.; Spotnitz, R. M.; Lundquist, J. T. TL 1987, 28, 1067.

Tsuneo Imamoto

Chiba University, Japan

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