Premium
3,5‐Bis( n ‐perfluorooctyl)benzyltriethylammonium Bromide (F‐TEBA): An Efficient, Easily Recoverable Fluorous Catalyst for Solid‐Liquid PTC Reactions
Author(s) -
Pozzi Gianluca,
Mihali Voichiţa,
Foschi Francesca,
Penso Michele,
Quici Silvio,
Fish Richard H.
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900631
Subject(s) - chemistry , bromide , catalysis , triethylamine , phase transfer catalyst , chloride , salt (chemistry) , organic chemistry
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.