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Issue 3, 2016
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Organic synthesis in fluoroalcohol-water two-phase systems

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Abstract

The addition of organic reactants to aqueous solutions of hexafluoroisopropanol (HFIP) leads to the formation of a two-phase system with one phase enriched in HFIP and the organic reactant and another largely aqueous phase. These systems were used as a reaction medium for Friedel–Crafts reactions between arenes and heteroarenes with a benzyl chloride electrophile. Good to excellent yields were obtained for nucleophiles of varying strength in the presence of large amounts of water (10–20 % HFIP v/v), which is unusual for weaker nucleophiles. Surprisingly, the reactions performed in the two-phase systems outperformed those in pure (100%) HFIP. The presence of the aqueous phase offers advantages over single-phase reaction media in terms of driving the reaction and product recovery. This system offers a new, largely aqueous medium for organic synthesis.

Graphical abstract: Organic synthesis in fluoroalcohol-water two-phase systems

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Publication details

The article was received on 29 Jun 2015, accepted on 08 Sep 2015 and first published on 11 Sep 2015


Article type: Communication
DOI: 10.1039/C5GC01463H
Author version available: Download Author version (PDF)
Citation: Green Chem., 2016,18, 681-685
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    Organic synthesis in fluoroalcohol-water two-phase systems

    N. Weisner and M. G. Khaledi, Green Chem., 2016, 18, 681
    DOI: 10.1039/C5GC01463H

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