Nucleophilic tetrafluoroethylation of carbonyl compounds with fluorinated sulfones

• Nucleophilic addition of PhSO2CF2CF2SiR3 to carbonyl compounds was studied.
• Desulfonylation of the adducts provided CF2CF2H-substituted alcohols.
• The same alcohols were prepared in one step using PhSO2CF2CF2H.

Global interest in the “CF2CF2” building blocks (tetrafluoroethylene, tetrafluoroethyl) is still rather marginal. One of the main reasons is the lack of efficient and selective tetrafluoroethylation reagents. In this context, we present here three new reagents (PhSO2CF2CF2R, R = SiMe3, SiEt3 and H) capable of nucleophilic addition to carbonyl compounds, thus affording rare alcohols containing the CF2CF2 motif. The experimental observations are complemented with a brief computational study which confirmed that the reactivity of the nucleophilic reagents is strongly dependent on electronic properties of substituents on both ends of the CF2CF2 group.

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