Pd-IHept-Catalyzed Ring-Opening of <i>gem</i>-Difluorocyclopropanes with Malonates Via Selective C–C Bond Cleavage: Synthesis of Monofluoroalkenes
Yuxuan Yan, Huijun Qian, Leiyang Lv, Zhiping Li
Abstract
Monofluoroalkene scaffolds are frequently found in various functional molecules. Herein, we report a Pd-IHept-catalyzed (NHC = N-heterocyclic carbene) defluorinative functionalization approach for the synthesis of monofluoroalkenes from gem -difluorocyclopropanes and malonates. The flexible yet sterically hindered N, N ′-bis(2,6-di(4-heptyl)phenyl)imidazol-2-ylidene ligand plays a key role in ensuring the high reaction efficiency. In addition, sterically hindered 1,1- and 1,2-disubstituted gem -difluorocyclopropanes could also be used in this transformation.
Topics & Concepts
ChemistrySteric effectsCarbeneRing (chemistry)CatalysisCombinatorial chemistryBond cleavageLigand (biochemistry)Cleavage (geology)Surface modificationMedicinal chemistryMoleculeStereochemistryOrganic chemistryReceptorEngineeringGeotechnical engineeringFracture (geology)Physical chemistryBiochemistryFluorine in Organic ChemistryCyclopropane Reaction MechanismsN-Heterocyclic Carbenes in Organic and Inorganic Chemistry