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Exploiting hexafluoroisopropanol (HFIP) in Lewis and Brønsted acid-catalyzed reactions

Abstract : Hexafluoroisopropanol (HFIP) is a solvent with unique properties that has recently gained attention for promoting a wide range of challenging chemical reactions. It was initially believed that HFIP was almost exclusively involved in the stabilization of cationic intermediates, owing to its high polarity and low nucleophilicity. However, in many cases, the mechanism of action of HFIP appears to be more complex. Recent findings reveal that many Lewis and Brønsted acid-catalyzed transformations conducted in HFIP additionally involve cooperation between catalyst and HFIP hydrogen-bond clusters, akin to Lewis-or Brønsted acid-assisted-Brønsted acid catalysis. This feature article showcases the remarkable versatility of HFIP in Lewis and Brønsted acid-catalyzed reactions, with an emphasis on examples yielding mechanistic insight.
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https://hal.archives-ouvertes.fr/hal-02990301
Contributor : David Leboeuf Connect in order to contact the contributor
Submitted on : Monday, November 23, 2020 - 2:37:41 PM
Last modification on : Saturday, July 3, 2021 - 12:13:45 AM
Long-term archiving on: : Wednesday, February 24, 2021 - 7:23:29 PM

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Valentyn Pozhydaiev, Martin Power, Vincent Gandon, Joseph Moran, David Lebœuf. Exploiting hexafluoroisopropanol (HFIP) in Lewis and Brønsted acid-catalyzed reactions. Chemical Communications, Royal Society of Chemistry, 2020, 56 (78), pp.11548-11564. ⟨10.1039/D0CC05194B⟩. ⟨hal-02990301⟩

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