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HFIP in Organic Synthesis

Journal

CHEMICAL REVIEWS
Volume 122, Issue 15, Pages 12544-12747

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.chemrev.1c00749

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Funding

  1. UNC Eshelman School of Pharmacy
  2. Higuchi Biosciences Center at the University of Kansas

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HFIP is a polar solvent that is widely used in organic synthesis for stabilizing ionic species, transferring protons, and engaging in various intermolecular interactions.
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.

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