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 / G. Pozzi, V. Mihali, F. Foschi, M. Penso, S. Quici, R. H. Fish. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 351:18(2009 Dec), pp. 3072-3076. [10.1002/adsc.200900631]

3,5-Bis(n-perfluorooctyl)benzyltriethylammonium Bromide (F-TEBA) : an efficient, easily recoverable fluorous catalyst for solid-liquid PTC reactions

V. Mihali
Secondo
;
F. Foschi;
2009-12

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.
Alkylation; Amino acids; Fluorous catalysis; Onium salts; Phase-transfer catalysis
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/145977
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