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

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 fluoro...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2009-12, Vol.351 (18), p.3072-3076
Main Authors: Pozzi, Gianluca, Mihali, Voichiţa, Foschi, Francesca, Penso, Michele, Quici, Silvio, Fish, Richard H.
Format: Article
Language:English
Subjects:
alkylation
amino acids
fluorous catalysis
onium salts
phase-transfer catalysis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200900631