Stereoselective Synthesis of Difluorinated 1,3-Dienes via Palladium-Catalyzed C–F Bond Activation of Tetrasubstituted <i>gem</i>-Difluoroalkenes
Yanhui Wang, Qiao Ma, Gavin Chit Tsui
Abstract
A highly diastereoselective Pd(0)-catalyzed synthesis of difluorinated 1,3-dienes is described. Symmetrical 1,3-dienes containing a vicinal difluoro moiety can be obtained as single diastereomers from tetrasubstituted gem-difluoroalkenes. The reaction presumably proceeds through a stereoselective twofold Pd-catalyzed Miyaura borylation/Suzuki–Miyaura cross-coupling of the C–F bond. Moreover, modular synthesis of unsymmetrical difluorinated 1,3-dienes is also achievable by the coupling between gem-difluoroalkenes and borylated monofluoroalkenes.
Topics & Concepts
ChemistryStereoselectivityMoietyCatalysisBorylationDiastereomerPalladiumVicinalCombinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryArylAlkylFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions