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Hexafluoroisopropanol as a highly versatile solvent

Nature Reviews Chemistry volume 1, Article number: 0088 (2017) Cite this article

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Abstract

1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) has recently become a very popular solvent or additive with applications across the spectrum of chemistry. Analysis shows that it possesses a wide range of interesting and unique properties. In this Perspective, we detail the main uses of HFIP in the natural sciences and disclose the underlying principles that give it such wide appeal. Accordingly, we show the broad usage and beneficial effects in many areas of chemistry.

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Figure 1: Use of HFIP in oxidation reactions with H2O2.
Figure 2: Selected examples of the reactivity of organic molecules based on the functional group or reagent that HFIP can activate.
Figure 3: Metal-free C–H bond activation has been reported when using HFIP as a solvent.
Figure 4: The use of HFIP in electrochemical processes has become increasingly common in recent years.
Figure 5: Selected examples of organometallic species used in combination with HFIP.
Figure 6: Applications of HFIP in chemical biology.
Figure 7: Supramolecular, polymer and materials chemistry influenced by HFIP solvent.

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Acknowledgements

The authors thank GlaxoSmithKline, the Engineering and Physical Sciences Research Council (EPSRC) and the People Programme (Marie Curie Actions) of the European Union's Seventh Framework Programme (Grant No. FP7/2007-2013) for funding. A.E.R.C. is grateful to the EPSRC Centre for Doctoral Training in Synthesis for Biology and Medicine (Grant No. EP/L015838/1) for a studentship, generously supported by AstraZeneca, Diamond Light Source, Defence Science and Technology Laboratory, Evotec, GlaxoSmithKline, Janssen, Novartis, Pfizer, Syngenta, Takeda, UCB and Vertex. The authors thank R. G. Compton and C. Batchelor-McAuley for helpful discussions.

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  1. Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, OX1 3TA, UK

    Ignacio Colomer, Anna E. R. Chamberlain, Maxwell B. Haughey & Timothy J. Donohoe

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  1. Ignacio Colomer
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  2. Anna E. R. Chamberlain
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  3. Maxwell B. Haughey
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All authors contributed to all aspects of article research, writing and editing. A.E.R.C. and M.B.H. contributed equally to this work.

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Correspondence to Ignacio Colomer or Timothy J. Donohoe.

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Colomer, I., Chamberlain, A., Haughey, M. et al. Hexafluoroisopropanol as a highly versatile solvent. Nat Rev Chem 1, 0088 (2017). https://doi.org/10.1038/s41570-017-0088

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