Diversity-Oriented Approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-Substituted Arenes from 1-(Diazo-2,2,2-trifluoroethyl)arenes
2014
Emer, Enrico | Twilton, Jack | Tredwell, Matthew | Calderwood, Samuel | Collier, Thomas Lee | Liégault, Benoît | Taillefer, Marc | Gouverneur, Véronique
Arenes substituted with perfluoroalkyl groups are attractive targets for drug and agrochemical development. Exploiting the carbenic character of donor/acceptor diazo compounds, a diversity-oriented synthesis of perfluoroalkylated arenes, for late stage fluorofunctionalization, is described. The reaction of 1-(diazo-2,2,2-trifluoroethyl)arenes with HF, F/Br, F₂, CF₃H, and CF₃SH sources give direct access to a variety of perfluoroalkyl-substituted arenes presenting with incremental fluorine content. The value of this approach is also demonstrated for radiochemistry and positron emission tomography with the [¹⁸F]-labeling of CF₃CHF-, CF₃CBrF-, and CF₃CF₂-arenes from [¹⁸F]fluoride.
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