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Synthesis of novel fluorous pyridinium ionic liquids

Synthesis of novel fluorous pyridinium ionic liquids The synthesis of a novel class of fluorous ionic liquids was investigated. The 2,6‐diperfluoroalkyl‐substituted pyridinium salts 2b‐f were solids at ambient temperature and insoluble in perfluoromethylcyclohexane. The addition of much further fluorous alkyl group to nitrogen atom of 2,6‐disubstituted pyridines 1 did not proceed to afford the pyridinium salts 3 having two or three perfluoroalkyl groups. On the other hand, the reaction of 3,5‐diperfluoroalkyl‐substituted pyridine 4 with perfluoroalkyl iodide proceeded to give N‐perfluoroalkylpyridinium salts 6a and 7a in good yields. Furthermore, the addition of tris(perfluoroalkyl)silylpropyl iodide afforded the corresponding pyridinium salt 8a excellently. The anion exchange of the resulting iodides gave the ionic liquids with high fluorophilicity. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

Synthesis of novel fluorous pyridinium ionic liquids

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References (25)

Publisher
Wiley
Copyright
"Copyright © 2018 Wiley Periodicals, Inc."
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.21464
Publisher site
See Article on Publisher Site

Abstract

The synthesis of a novel class of fluorous ionic liquids was investigated. The 2,6‐diperfluoroalkyl‐substituted pyridinium salts 2b‐f were solids at ambient temperature and insoluble in perfluoromethylcyclohexane. The addition of much further fluorous alkyl group to nitrogen atom of 2,6‐disubstituted pyridines 1 did not proceed to afford the pyridinium salts 3 having two or three perfluoroalkyl groups. On the other hand, the reaction of 3,5‐diperfluoroalkyl‐substituted pyridine 4 with perfluoroalkyl iodide proceeded to give N‐perfluoroalkylpyridinium salts 6a and 7a in good yields. Furthermore, the addition of tris(perfluoroalkyl)silylpropyl iodide afforded the corresponding pyridinium salt 8a excellently. The anion exchange of the resulting iodides gave the ionic liquids with high fluorophilicity.

Journal

Heteroatom ChemistryWiley

Published: Dec 1, 2018

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