Cobalt-Catalyzed Fluoroallyllation of Carbonyls via C–C Activation of <i>gem</i>-Difluorocyclopropanes
Yinan Ai, Hanlin Yang, Chunying Duan, Xingwei Li, Songjie Yu
Abstract
A new Co-catalyzed sequential C–C and C–F activation of gem-difluorinated cyclopropanes (gem-FCPs) to form nucleophilic fluoroallylcobalt, followed by addition to aldehydes, is reported. The protocol features the regioselective cleavage of dual chemical bonds of readily available gem-FCPs to prepare easily separable linear (Z)- and (E)-fluorinated homoallylic alcohols with a broad scope. This discovery established a new strategy for the efficient transformation of gem-FCPs as well as the synthesis of challenging fluorinated homoallylic alcohols.
Topics & Concepts
ChemistryCatalysisRegioselectivityNucleophileCobaltCombinatorial chemistryBond cleavageCleavage (geology)Nucleophilic additionAllylic rearrangementOrganic chemistryFracture (geology)Geotechnical engineeringEngineeringFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods