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Issue 99, 2015
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Ionic liquids as an electrolyte for the electro synthesis of organic compounds

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Abstract

The use of ionic liquids (ILs) as a solvent and an electrolyte for electro organic synthesis has been reviewed. To date several ILs exist, however the ILs based on tetraalkylammonium, pyrrolidinium, piperidinium and imidazolium cations with BF4, PF6, and TFSI anions have been widely used and explored the most. Electro organic synthesis in ionic liquid media leading to the synthesis of a wide range of organic compounds has been discussed. Anodic oxidation or cathodic reduction will generate radical cation or anion intermediates, respectively. These radicals can undergo self coupling or coupling with other molecules yielding organic compounds of interest. The cation of the IL is known to stabilize the radical anion extensively. This stabilization effect has a specific impact on the electrochemical CO2 reduction and coupling to various organics. The relative stability of the intermediates in IL leads to the formation of specific products in higher yields. Electrochemical reduction of imidazolium or thiazolium based ILs generates N-heterocyclic carbenes that have been shown to catalyze a wide range of base or nucleophile catalyzed organic reactions in IL media, an aspect that falls into the category of organocatalysis. Electrochemical fluorination or selective electrochemical fluorination is another fascinating area that delivers selectively fluorinated organic products in Et3nHF or Et4NF·nHF adducts (IL) via anodic oxidation. Oxidative polymerization in ILs has been explored the most; although morphological changes were observed compared to the conventional methods, polymers were obtained in good yields and in some cases ILs were used as dopants to improve the desired properties.

Graphical abstract: Ionic liquids as an electrolyte for the electro synthesis of organic compounds

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Article information


Submitted
19 Aug 2015
Accepted
21 Sep 2015
First published
23 Sep 2015

Chem. Commun., 2015,51, 17499-17516
Article type
Feature Article
Author version available

Ionic liquids as an electrolyte for the electro synthesis of organic compounds

M. Kathiresan and D. Velayutham, Chem. Commun., 2015, 51, 17499
DOI: 10.1039/C5CC06961K

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