Fluorinated building blocks are popular structural motifs, which become increasingly important in various areas, and most of all in drug discovery and agrochemistry. In our ongoing research in the scalable synthesis of medchem relevant fluorine-containing building blocks, we decided to focus our attention on –CF2-CF2- motif. Insertion of such moiety into the carbon chain significantly increased lipophilicity. Also, the last researches showed that the fragment is involved in multiple interactions with the enzyme. This study validates that the polar and hydrophobic character of -CF2−CF2- group can essentially improve the contacts between ligand and its host protein. We chose the functionalized (2,2,3,3-tetrafluorocyclobutyl)arenes as model objects for the investigation directed to the influence of this fragment on key parameters of building blocks for the medicinal chemistry.<br/>In our thesis, the methodology for the insertion of 2,2,3,3-tetrafluorocyclobutyl fragment to arenes will be presented. This procedure includes safe and efficient method of obtaining and using tetrafluorethilene (TFE) for [2+2] cycloaddition with styrenes. Also, the tolerance of the fragment for different classical reaction conditions of implementation and modification of functional groups will be discussed. The impact of the fragment to Physico-chemical parameters of the molecules compare to non-fluorinated analogs would be shown.

Functionalized (2,2,3,3-tetrafluorocyclobutyl)arenes – MedChem relevant building blocks

ACS Fall 2020 Virtual Meeting

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