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 reacted under mild conditions to give [3,5-bis(n-perfluorooctyl)benzyl]triethylammonium bromide (F-TEBA), an analog of the versatile phase-transfer catalyst, benzyltriethylammonium chloride (TEBA), contg. two fluorous pony tails. This perfluoroalkylated quaternary ammonium salt was successfully employed as a catalyst in a variety of reactions run under solid-liq. phase-transfer catalysis (SL-PTC) conditions. Thus, being both hydrophobic and lipophobic, F-TEBA could be quickly recovered in quant. yields, and reused without loss of activity over several reaction cycles.