Synthesis of fluorous pyrrolidinium and piperidinium ionic liquids

The synthesis of a novel class of fluorous ionic liquids was investigated. The reaction of pyrrolidine or piperidine with perfluoroalkyl iodide in pyridine proceeded to give the corresponding tertiary amine derivatives 3 and 4 in good yields. The following reaction of the resulting compounds 3 and 4 with methyl iodide gave the corresponding iodide salts 5a and 6a in high yields. On the other hand, a similar reaction with an excess amount of perfluoroalkyl iodide afforded iodide salts 7a and 8a possessing two perfluoroallcyl groups on nitrogen atom. The anion exchange of the resulting iodides gave the ionic liquids with high fluorophilicity. (C) 2017 Elsevier Ltd. All rights reserved.