HFIP in Organic Synthesis

1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability to stabilize ionic species, transfer protons, and engage in a range of other intermolecular interactions. The use of this solvent has expo...

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Bibliographic Details
Published in:Chemical reviews 2022-08, Vol.122 (15), p.12544-12747
Main Authors: Motiwala, Hashim F., Armaly, Ahlam M., Cacioppo, Jackson G., Coombs, Thomas C., Koehn, Kimberly R. K., Norwood, Verrill M., Aubé, Jeffrey
Format: Article
Language:English
Subjects:
Chemical reactions
Hydrogen bonds
Physical properties
Solvents
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Summary:1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability to stabilize ionic species, transfer protons, and engage in a range of other intermolecular interactions. The use of this solvent has exponentially increased in the past decade and has become a solvent of choice in some areas, such as C–H functionalization chemistry. In this review, following a brief history of HFIP in organic synthesis and an overview of its physical properties, literature examples of organic reactions using HFIP as a solvent or an additive are presented, emphasizing the effect of solvent of each reaction.
ISSN:0009-2665
1520-6890
DOI:10.1021/acs.chemrev.1c00749