Synthesis of an Eccentric Electron-Deficient Fluorinated Motif, Tetrafluoro-λ<sup>6</sup>-sulfanyl <i>gem</i>-Difluorocyclopropenes
Koki Maruno, Kiyoteru Niina, Osamu Nagata, Norio Shibata
Abstract
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-λ6-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.
Topics & Concepts
SulfanylChemistryElectrophileCycloadditionSurface modificationArylMotif (music)DifluorocarbeneCombinatorial chemistryStereochemistryStructural motifMedicinal chemistryOrganic chemistryPhysicsAlkylCatalysisAcousticsBiochemistryPhysical chemistryFluorine in Organic ChemistrySynthesis and Reactions of Organic CompoundsClick Chemistry and Applications