Synthesis of an Eccentric Electron-Deficient Fluorinated Motif, Tetrafluoro-λ6 -sulfanyl gem-Difluorocyclopropenes

Fluoro-functionalization is now recognized as a critical strategy in drug discovery; however, the accessible fluoro-functional groups are limited. We herein introduce an eccentric, fully fluorinated motif, trans-tetrafluoro-lambda(6)-sulfanyl gem-difluorocyclopropene 2. This novel motif is highly lipophilic and polarized, enabling a connection of two independent groups via three continuous atoms with a large angle of pseudo cis configuration. The target motif was synthesized via a [2+1] cycloaddition of electron-deficient (hetero)aryl-SF4-alkynes 1 with an electrophilic difluorocarbene source.

Automated summary

In this study, a fully fluorinated motif with high lipophilicity and polarity was introduced, which can connect two independent groups via three continuous atoms. The motif was synthesized through a cycloaddition reaction.