CE07 - Chimie moléculaire

Expanding the Hammett acidity scale to fluorinating reagents – HAMAC

Submission summary

The importance of organofluorine chemistry in modern life is undisputable. In fact, around 20% of marketed drugs and 50% of agrochemicals contain fluorine atoms. In this context, numerous fluorination methods have been developed over the last decades thanks to the availability of powerful reagents such as Selectfluor®, Accufluor® or Deoxofluor®. However, all these reagents (nucleophilic or electrophilic) originate from a single source of fluorine that is hydrogen fluoride. While anhydrous hydrogen fluoride (aHF) is rarely exploited as such in academia for the development of new transformations, it is used on large scale in industry for the preparation of high-valued synthons (e.g. Balz-Schiemann reaction, Swarts halogen exchange). Moreover, aHF displays several remarkable features as it turns into powerful fluorinating medium when combined with organic bases while its association with Lewis acids produces the strongest known superacids. However, evaluating the acidity of aHF-based solutions is still a major challenge and no general methods have been developed so far. We believe that a better understanding of the acidic properties of such media is essential for the development of new atom-economic fluorination processes.

The main objectives of this project will be to develop a new method combining NMR analyses and DFT calculations to determine the Hammett acidity function of aHF-based media and to exploit this method to gain better insights into the reactivity of such fluorinating reagents.

Project coordination

Bastien MICHELET (Institut de Chimie des Milieux et des Matériaux de Poitiers)

The author of this summary is the project coordinator, who is responsible for the content of this summary. The ANR declines any responsibility as for its contents.

Partner

IC2MP Institut de Chimie des Milieux et des Matériaux de Poitiers

Help of the ANR 218,090 euros
Beginning and duration of the scientific project: September 2022 - 48 Months

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