FLP-Catalyzed Monoselective C–F Functionalization in Polyfluorocarbons at Geminal or Distal Sites
Richa Gupta, Dipendu Mandal, Amit K. Jaiswal, Rowan D. Young
Abstract
We report frustrated Lewis pair (FLP)-catalyzed monoselective C–F activation in a range of aliphatic polyfluorocarbons with equivalent geminal and distal C–F positions. This methodology can be applied to aromatic-, ether-, thioether-, and alkyl-supported fluoromethyl groups. We expand the range of FLP base partners that work with monoselective C–F activation to include sulfide. The activated products can be subsequently functionalized via SN2 substitutions, photoredox-alkylations, and Suzuki couplings.
Topics & Concepts
GeminalChemistryThioetherCatalysisAlkylSurface modificationFrustrated Lewis pairStereochemistrySulfideEtherMedicinal chemistryLewis acids and basesOrganic chemistryPhysical chemistryFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsOrganoboron and organosilicon chemistry