Palladium-Catalyzed Allylic C–F Bond Functionalization of Pentafluoroethyl Alkenes with Heteroatom Nucleophiles
Zhengjie Fu, Gavin Chit Tsui
Abstract
High Resolution Image Download MS PowerPoint Slide A diastereoselective Pd-catalyzed allylic C–F bond functionalization of pentafluoroethyl alkenes is described. Heteroatom nucleophiles including amines, alcohols, and thiols can be employed to construct new C–N, C–O, or C–S bonds with concomitant cleavage of an allylic C–F bond. Both 1,1- and 1,2-disubstituted pentafluoroalkenes can be utilized to synthesize novel tetra- and trisubstituted alkenes containing an sp 2 -carbon connected to both F and CF 3 in good to excellent diastereoselectivities.
Topics & Concepts
ChemistryNucleophileAllylic rearrangementSurface modificationPalladiumCatalysisHeteroatomMedicinal chemistryOrganic chemistryCombinatorial chemistryRing (chemistry)Physical chemistryFluorine in Organic ChemistryCyclopropane Reaction Mechanisms