Collect. Czech. Chem. Commun. 2003, 68, 1039-1045

Synthesis of Polyfluorinated Alkynes, Novel Building Blocks for Fluorous Chemistry

Tomáš Bříza, Jaroslav Kvíčala* and Oldřich Paleta

Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic


Ethynyldimethylphenylsilane (2) was lithiated with butyllithium and reacted with (perfluorohexyl)ethyl triflate (1) to afford silylated 4-(perfluorohexyl)butyne 3, which was deprotected with potassium fluoride to give 4-(perfluorohexyl)butyne 4. Lithiation of fluoroalkyne 4 with butyllithium followed by the addition of polyfluoroalkyl triflate 1 furnished bis(perfluorohexyl)butyne 5 in a moderate yield. Polyfluoroalkylated alkynes 3, 4 and 5 are perspective building blocks for fluorous chemistry, the sufficient nucleophilic properties of which are preserved by one or two ethylene spacers between the triple bond and perfluoroalkyl group(s).

Keywords: Fluorous ligands; Acetylenes; Alkynes; Acetylides; Polyfluoroalkyl groups; Fluorophilic; Nucleophilic substitutions; Lithiations.

References: 34 live references.