Nickel‐Catalyzed Intramolecular Alkene Difunctionalization by Ball‐Milling
Matthew T. J. Williams, Louis C. Morrill, Duncan L. Browne
Abstract
Abstract A mechanochemical nickel‐catalyzed intramolecular difunctionalization reaction of alkene tethered aryl halides with alkyl halides is herein described. This method allows for synthesis of 3,3‐disubstituted heterocycles, namely oxindoles, with shorter reaction times than solution‐phase counterparts. Additionally, this process is solvent minimized, with DMA used in liquid‐assisted grinding (LAG) quantities and circumvents the need for chemical activation of the terminal reductant (manganese) through mechanical grinding. The process can be scaled up to yield over a gram of product and modest enantioinduction is possible by utilizing a chiral PyrOx ligand. magnified image
Topics & Concepts
ChemistryIntramolecular forceAlkeneNickelCatalysisHalideArylAlkylBall millCombinatorial chemistryGrindingLigand (biochemistry)Organic chemistryChemical engineeringMetallurgyMaterials scienceBiochemistryReceptorEngineeringCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsOrganoboron and organosilicon chemistry