A readily available 3,5-bis(perfluorooctyl)benzyl bromide and triethylamine were reacted under mild conditions to give 3,5-bis(n-perfluorooctyl)benzyltriethylammonium bromide (F-TEBA), an analogue of the versatile phase-transfer catalyst, benzyltriethylammonium chloride (TEBA), containing two fluorous ponytails. This perfluoroalkylated quaternary ammonium salt was successfully employed as a catalyst in a variety of reactions run under solid-liquid phase-transfer catalysis (SL-PTC) conditions. Thus, being both hydrophobic and lipophobic, F-TEBA could be quickly recovered in quantitative yields, and reused without loss of activity over several reaction cycles.

3,5-Bis(n-perfluorooctyl)benzyltriethylammonium Bromide (F-TEBA): An Efficient, Easily Recoverable Fluorous Catalyst for Solid-Liquid PTC Reactions

FOSCHI F;
2009-01-01

Abstract

A readily available 3,5-bis(perfluorooctyl)benzyl bromide and triethylamine were reacted under mild conditions to give 3,5-bis(n-perfluorooctyl)benzyltriethylammonium bromide (F-TEBA), an analogue of the versatile phase-transfer catalyst, benzyltriethylammonium chloride (TEBA), containing two fluorous ponytails. This perfluoroalkylated quaternary ammonium salt was successfully employed as a catalyst in a variety of reactions run under solid-liquid phase-transfer catalysis (SL-PTC) conditions. Thus, being both hydrophobic and lipophobic, F-TEBA could be quickly recovered in quantitative yields, and reused without loss of activity over several reaction cycles.
2009
alkylation; amino acids; fluorous catalysis; onium salts; phase-transfer catalysis
Pozzi, G; Mihali, V; Foschi, F; Penso, M; Quici, S; Fish, R. H.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11383/2086293
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